EP1938685A1 - Insecticidal and bactericidal composition - Google Patents
Insecticidal and bactericidal composition Download PDFInfo
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- EP1938685A1 EP1938685A1 EP06781253A EP06781253A EP1938685A1 EP 1938685 A1 EP1938685 A1 EP 1938685A1 EP 06781253 A EP06781253 A EP 06781253A EP 06781253 A EP06781253 A EP 06781253A EP 1938685 A1 EP1938685 A1 EP 1938685A1
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- phenyl
- heptafluoro
- dimethyl
- dibromo
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
Definitions
- the present invention relates to a novel insecticidal and fungicidal composition exhibiting excellent insecticidal and fungicidal actions for the labor-saving control of crop diseases and insect pests.
- the compound represented by the general formula (1) of the present invention is a novel compound having an insecticidal activity.
- these active compounds have an action exhibiting any of an insecticidal effect or a fungicidal effect with the use of a single agent thereof, but cannot control crop diseases and insect pests at the same time.
- Patent Document 1 International Publication No. 2000 / 55120 pamphlet
- Patent Document 2 US Patent No. 6548514
- Patent Document 3 International Publication No. 2000 / 7980 pamphlet
- Patent Document 4 US Patent Laid-Open No. 2002-032238
- Patent Document 5 International Publication No. 2005 / 21488 pamphlet
- Patent Document 6 International Publication No. 2003 / 8372 pamphlet
- Patent Document 7 International Publication No. 2005 / 42474 pamphlet
- the present invention is to provide an insecticidal and fungicidal composition capable of controlling crop diseases and insect pests at the same time by combining an insecticidal active ingredient and a fungicidal active ingredient.
- an insecticidal and fungicidal composition containing one or more compounds represented by the general formula (1) or (2) as insecticidal active ingredients, and one or more compounds represented by the general formula (3) or (4) as fungicidal active ingredients has excellent insecticidal and fungicidal effects on crop diseases and insect pests.
- the present invention has been completed.
- X 1 is a hydrogen atom or a fluorine atom
- R 1 and R 2 are independently a hydrogen atom or a C1-C4 alkyl group
- Q 1 is a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a
- Y 1 and Y 5 may be the same or different and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y 3 represents a C2-C6 perfluoroalkyl group, a C2-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulf
- X 2 is a hydrogen atom or a fluorine atom
- R 4 and R 5 are independently a hydrogen atom or a C1-C4 alkyl group
- R 3 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group,
- E 1 represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group or a C3-C4 haloalkynylene group
- R 6 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group or a C2-C6 haloalkynyl group
- E 2 represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group or a C3-C4 haloalkynylene group
- R 8 represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group,
- Y 6 and Y 10 may be the same or different and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y 8 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfulfonyl group or
- R11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group or a heterocyclic alkyl group
- R12 and R17 independently represent a hydrogen atom
- R13 and R14 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
- R15 and R16 independently represent a hydrogen atom
- R18 represents an aryl group or a heterocycle, or
- R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen or an alkenyl group having 2 to 6 carbon atoms substituted with halogen
- R22 and R27 independently represent a hydrogen atom
- R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
- R25 and R26 independently represent a hydrogen atom
- R28 represents an aryl group or a heterocycle
- an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (1) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (3) as set forth in [1] as active ingredients;
- an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (1) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (4) as set forth in [1] as active ingredients;
- an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (2) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (3) as set forth in [1] as active ingredients; and
- an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (2) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (4) as set forth in [1] as active ingredients.
- the nursery box treatment of paddy rice using the insecticidal and fungicidal composition of the present invention is helpful in decreasing the amount of a liquid chemical per unit area and reducing the influence on the environment as well as in reducing burden of a farmhouse's labor. Furthermore, it is further helpful in saving much labor by mixing with a fertilizer and carrying out fertilizer application at the time of rice transplantation or setting. Accordingly, the insecticidal and fungicidal composition of the present invention is extremely effective in control of diseases and insect pests at the same time, and saving labor for agricultural products, and horticultural products, and provides technical inventiveness which is also excellent in industrial effectiveness.
- insecticidal and fungicidal composition of the present invention is capable of the labor-saving control of diseases and insect pests at the same time.
- halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
- C1-Cb (a and b represent an integer of not less than 1)
- C1-C3 refers to 1 to 3 carbon atoms
- C2-C6 refers to 2 to 6 carbon atoms
- C1-C4" refers to 1 to 4 carbon atoms.
- n- refers to normal, "i-” refers to iso, "s-" refers to secondary and "t-" refers to tertiary.
- C1-C3 alkyl group represents, for example, linear, branched or cyclic alkyl groups having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, cyclopropyl and the like.
- the "C1-C4 alkyl group” represents, for example, linear or branched alkyl groups having 1 to 4 carbon atoms such as n-butyl, s-butyl, i-butyl, t-butyl and the like, in addition to "C1-C3 alkyl group.”
- the "C1-C6 alkyl group” represents, for example, linear or branched alkyl groups having 1 to 6 carbon atoms such as n-pentyl, 2-pentyl, 3-pentyl, neopentyl, n-hexyl, 2-hexyl, 4-methyl-2-pentyl, 3-methyl-n-pentyl and the like, in addition to "C1-C4 alkyl group.”
- C1-C3 haloalkyl group represents, for example, linear or branched alkyl groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2-dibromoethyl, 2,2,2-tribromoethyl, 2-iodoethyl, pentafluoroe
- C1-C4 haloalkyl group represents, for example, linear or branched alkyl groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 4-fluoro-n-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl and the like, in addition to “C1-C3 haloalkyl group.”
- the "C1-C6 haloalkyl group” represents, for example, linear or branched alkyl groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
- C2-C4 alkenyl group represents, for example, alkenyl groups of 2 to 4 carbon atoms having a double bond in the carbon chain such as vinyl, allyl, 2-butenyl, 3-butenyl and the like
- C2-C6 alkenyl group represents, for example, alkenyl groups of 2 to 6 carbon atoms having a double bond in the carbon chain.
- C2-C4 haloalkenyl group represents, for example, linear or branched alkenyl groups of 2 to 4 carbon atoms having a double bond in the carbon atom substituted with one or more halogen atoms which may be the same or different, such as 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4,4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl and the like, and the "C2-C6 haloalkenyl group” represents, for example, linear or branched alkenyl groups of 2 to 6 carbon atoms having a double bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.
- C2-C4 alkynyl group represents, for example, linear or branched alkynyl groups of 2 to 4 carbon atoms having a triple bond in the carbon chain such as propargyl, 1-butyne-3-yl, 1-butyne-3-methyl-3-yl and the like
- C2-C6 alkynyl group represents, for example, linear or branched alkynyl groups of 2 to 6 carbon atoms having a triple bond in the carbon chain.
- C2-C4 haloalkynyl group represents, for example, linear or branched alkenyl groups of 2 to 4 carbon atoms having a triple bond in the carbon chain substituted with one or more halogen atoms which may be the same or different
- C2-C6 haloalkynyl group represents, for example, linear or branched alkenyl groups of 2 to 6 carbon atoms having a triple bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.
- C3-C6 cycloalkyl group represents, for example, cycloalkyl groups of 3 to 6 carbon atoms having a cyclic structure, such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl and the like
- C3-C8 cycloalkyl group represents, for example, cycloalkyl groups of 3 to 8 carbon atoms having a cyclic structure.
- C3-C6 halocycloalkyl group represents, for example, cycloalkyl groups of 3 to 6 carbon atoms having a cyclic structure substituted with one or more halogen atoms which may be the same or different, such as 2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, 4-chlorocyclohexyl and the like
- C3-C8 halocycloalkyl group represents, for example, cycloalkyl groups of 3 to 8 carbon atoms having a cyclic structure substituted with one or more halogen atoms which may be the same or different.
- C1-C3 alkoxy group represents, for example, linear or branched alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy and the like, and the "C1-C6 alkoxy group” represents linear or branched alkoxy groups having 1 to 6 carbon atoms.
- the "C1-C3 haloalkoxy group” represents, for example, linear or branched haloalkoxy groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 3-fluoro-n-propyloxy and the like
- the "C1-C4 haloalkoxy group” represents, for example, linear or branched haloalkoxy groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 1,1,1,3,3,4,4,4-octafluoro-2-butyloxy and the like, in addition to "C1-C3 haloalkoxy group," and the "C1-C6 haloalkoxy group” represents, for example, linear or branche
- the "C1-C3 alkylthio group” represents, for example, linear, branched or cyclic alkylthio groups having 1 to 3 carbon atoms such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio and the like
- the "C1-C4 alkylthio group” represents, for example, linear, branched or cyclic alkylthio groups having 1 to 4 carbon atoms such as n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio and the like
- the "C1-C6 alkylthio group” represents, for example, linear or branched alkylthio groups having 1 to 6 carbon atoms.
- C1-C3 haloalkylthio group represents, for example, linear or branched alkylthio groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio and the like.
- C1-C4 haloalkylthio group represents, for example, linear or branched alkylthio groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as nonafluoro-n-butylthio, nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio and the like, in addition to "C1-C3 haloalkylthio group,” and the "C1-C6 haloalkylthio group” represents, for example, linear or branched alkylthio groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
- C1-C3 alkylsulfinyl group represents, for example, linear, branched or cyclic alkylsulfinyl groups having 1 to 3 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl and the like, and the "C1-C6 alkylsulfinyl group” represents linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms.
- C1-C3 haloalkylsulfinyl group represents, for example, linear or branched alkylsulfinyl groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl', heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl and the like, and the "C1-C6 haloalkylsulfinyl group” represents, for example, linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
- C1-C3 alkylsulfonyl group represents, for example, linear, branched or cyclic alkylsulfonyl groups having 1 to 3 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl and the like, and the "C1-C6 alkylsulfonyl group” represents linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms.
- C1-C3 haloalkylsulfonyl group represents, for example, linear or branched alkylsulfonyl groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl and the like, and the "C1-C6 haloalkylsulfonyl group” represents, for example, linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
- C1-C4 alkylamino group represents, for example, linear, branched or cyclic alkylamino groups having 1 to 4 carbon atoms, such as methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, cyclopropylamino and the like
- the "di C1-C4 alkylamino group” represents, for example, linear or branched amino groups substituted with two alkyl groups having 1 to 4 carbon atoms which may be the same or different, such as dimethylamino, diethylamino, N-ethyl-N-methylamino and the like.
- C1-C4 alkylcarbonyl group represents, for example, linear, branched or cyclic alkylcarbonyl groups having 1 to 4 carbon atoms, such as formyl, acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl and the like.
- C1-C4 haloalkylcarbonyl group include linear or branched alkylcarbonyl groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, iodoacetyl, 3,3,3-trifluoropropionyl, 2,2,3,3,3-pentafluoropropionyl and the like.
- C1-C4 alkylcarbonyloxy group represents, for example, linear or branched alkylcarbonyloxy groups having 1 to 4 carbon atoms, such as acetoxy, propionyloxy and the like.
- C1-C4 alkoxycarbonyl group represents, for example, linear or branched alkoxycarbonyl groups having 1 to 4 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl and the like.
- C1-C4 perfluoroalkyl group represents, for example, linear or branched alkyl groups having 1 to 4 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl and the like
- the "C2-C6 perfluoroalkyl group” represents, for example, linear or branched alkyl groups having 2 to 6 carbon atoms which are all substituted with fluorine atoms, such as pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluorine
- C1-C6 perfluoroalkylthio group represents, for example, linear or branched alkylthio groups having 1 to 6 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethylthio, pentafluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio, nonafluoro-i-butylthio, perfluoro-n-pentylthio, perfluoro-n-hexylthio and the like.
- C1-C6 perfluoroalkylsulfinyl group represents, for example, linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2-butylsulfinyl, nonafluoro-i-butylsulfinyl, perfluoro-n-pentylsulfinyl, perfluoro-n-hexylsulfinyl and the like.
- C1-C6 perfluoroalkylsulfonyl group represents, for example, linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, nonafluoro-2-butylsulfonyl, nonafluoro-i-butylsulfonyl, perfluoro-n-pentylsulfonyl, perfluoro-n-hexylsulfonyl and the like.
- the "C1-C4 alkylene group” represents, for example, linear or branched alkylene groups having 1 to 4 carbon atoms such as methylene, ethylene, propylene, dimethylmethylene, isobutylene and the like.
- the "C2-C4 alkenylene group” represents, for example, linear or branched alkenylene groups of 2 to 4 carbon atoms having a double bond in the carbon atom.
- the "C3-C4 alkynylene group” represents, for example, linear or branched alkynylene groups of 3 to 4 carbon atoms having a triple bond in the carbon chain.
- the "C1-C4 haloalkylene group” represents, for example, linear or branched alkylene groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as chloromethylene, chloroethylene, dichloromethylene, difluoromethylene and the like.
- the "C2-C4 haloalkenylene group” represents, for example, linear or branched alkynylene groups of 2 to 4 carbon atoms having a double bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.
- C3-C4 haloalkynylene group represents, for example, linear or branched alkynylene groups of 3 to 4 carbon atoms having a triple bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.
- the compounds represented by the general formulae (1) and (2) of the present invention contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula in some cases and have two or more optical isomers in some cases. However, the present invention also includes all of the respective optical isomers and mixtures consisting of these isomers in any ratio. Furthermore, the compounds represented by the general formulae (1) and (2) of the present invention have two or more geometrical isomers derived from a carbon-carbon double bond in its structural formula in some cases. However, the present invention also includes all of the respective geometrical isomers and mixtures consisting of these isomers in any ratio.
- R 1 is preferably a hydrogen atom or a C1-C4 alkyl group and further preferably a hydrogen atom, a methyl group or an ethyl group.
- R 2 is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- R 4 is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- R 5 is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- X 1 is preferably a hydrogen atom or a fluorine atom.
- X 2 is preferably a hydrogen atom or a fluorine atom.
- Q 1 is preferably a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsul
- Q 2 is preferably is a substituted phenyl group represented by the general formula (A).
- Y 1 and Y 5 are preferably independently a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group or a cyano group;
- Q 3 is preferably a substituted phenyl group represented by the general formula (B).
- Y 6 and Y 10 are preferably independently a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group or a cyano group; Y
- alkyl group having 1 to 6 carbon atoms examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and the like.
- alkenyl group having 2 to 6 carbon atoms examples include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group and the like.
- alkyl group having 1 to 6 carbons substituted with halogen examples include chlorine substituted alkyl groups such as a chloromethyl group, a 2-chloroethyl group, a 2,2,2-trichloroethyl group, a 3-chloro-1-propyl group, a 4-chloro-1-butyl group and the like; fluorine substituted alkyl groups such as a 2-fluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,1,3,3,3-hexafluoro-2-propyl group, a 1,3-difluoro-2-propyl group, a 5-fluoro-1-pentyl group, a 6,6,6,5,5,4,4,3,3-nonafluoro-1-hexyl group, a 1-ethoxy-2,2,2-trifluoroethyl group and the like; bromine substituted alkyl groups such as a 2-bromoethyl group.,
- Examples of the cycloalkyl group having 3 to 6 carbons substituted with halogen include chlorine substituted cycloalkyl groups such as a chlorocyclopropyl group, a 2-chlorocyclobutyl group, a 2-chlorocyclopentyl group, a 2-chlorocyclohexyl group, a 3-chlorocyclohexyl group, a 4-chlorocyclohexyl group and the like; fluorine substituted cycloalkyl groups such as a 2-fluorocyclohexyl group, a 2,2,3,3-tetrafluorocyclopropyl group and the like; bromine substituted cycloalkyl groups such as a 2-bromocyclohexyl group and the like; and iodine substituted cycloalkyl groups such as a 2-iodocyclohexyl group and the like.
- chlorine substituted cycloalkyl groups such as a chlorocyclopropy
- alkenyl group having 2 to 6 carbons substituted with halogen examples include chlorine substituted alkenyl group such as a 2-chloro-2-propenyl group, a 5-chloro-4-pentenyl group and the like; and fluorine substituted alkenyl groups such as a 4,4,4-trifluoro-2-butenyl group, a 6,6,6-trifluoro-5-hexenyl and the like.
- aryl group examples include a phenyl group, a naphthyl group and the like.
- heterocycle examples include a pyridyl group, a pyrimidyl group, a thienyl group, a furanyl group, a pyrazolyl group, an imidazolyl group, an isothiazolyl group, an isoxazolyl group, an indolyl group, a quinolyl group, a benzofuranyl group, a benzothienyl group, a benzoxazolyl group, a benzoisoxazolyl group, a benzimidazoly group, a benzothiazolyl group, a benzoisothiazolyl group and the like.
- alkyl groups such as a.methyl group, an ethyl group, a propyl group, a butyl group and the like
- cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like
- halogen substituted alkyl groups such as a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group, a trifluoroethyl group and the like
- alkoxy groups such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like
- halogen substituted alkoxy groups such as a trifluoromethoxy group, a difluoromethoxy group, a trifluoroethoxy group and the like
- alkoxy groups such as a methoxy group, an ethoxy group, a propoxy
- Typical preparation methods of the compound represented by the general formula (1) are illustrated below and the compound represented by the general formula (1) can be prepared according to the preparation methods, but the preparation method paths are not restricted to the following preparation methods.
- Preferable substituents or atoms in the compounds represented by the general formulae shown in the following preparation methods are illustrated below.
- L is preferably a chlorine atom, a bromine atom or a hydroxy group.
- R 1 a is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- R 2 a is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- G 1 a and G 2 a are preferably independently an oxygen atom or a sulfur atom, and further preferably both of G 1 a and G 2 a are oxygen atoms.
- X 1 a is preferably a hydrogen atom or a halogen atom, and further preferably a hydrogen atom or a fluorine atom.
- X 2 a is preferably a hydrogen atom or a fluorine atom, and further preferably a hydrogen atom.
- X 3 a and X 4 a are preferably a hydrogen atom.
- Y 1 a and Y 5 a are preferably independently a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group or a cyano group.
- Y 2 a and Y 4 a are preferably a hydrogen atom, a halogen atom or a methyl group, and further preferably a hydrogen atom.
- Q 1 a is preferably a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkyl
- R a and R b are preferably independently a fluorine atom, a trifluoromethyl group, a pentafluoroethyl group or a heptafluoro-n-propyl group, and further preferably independently a fluorine atom, a trifluoromethyl group or a pentafluoroethyl group.
- R c is preferably a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, an ethoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group, a p-toluenesulfonyloxy group, an acetoxy group or a trifluoroacetoxy group, and further preferably a hydroxy group, a chlorine atom, a bromine atom, a methoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group or a p-toluenesulfonyloxy group, and further preferably a hydroxy group, a chlorine atom, a bromine atom, a methoxy group, a
- R c ' is preferably a hydroxy group.
- R c " is preferably a chlorine atom or a bromine atom.
- X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , Y 4 , Y 5 , G 1 , G 2 , R 1 , R 2 and Q 1 may independently correspond to X 1 a, X 2 a, X 3 a, X 4 a, Y 1 a, Y 2 a, Y 4 a, Y 5 a, G 1 a, G 2 a, R 1 a, R 2 a and Q 1 a, or vice versa.
- Q 2 represents the same as those in [1] or the general formula (A), (C) or (18),
- Y 11 and Y 14 may be the same or different and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y 13 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C2-C6 perfluoroalkylthio group, a C1
- a 1 , A 2 , A 3 , A 4 , G 1 , G 2 , R 1 , R 2 , X, n, Q 1 and Q 2 represent the same as those described above; and L represents a functional group having a leaving ability such as a halogen atom, a hydroxy group or the like.
- an aromatic carboxylic acid amide derivative having a nitro group represented by the general formula (21) By reacting an m-nitroaromatic carboxylic acid derivative having a leaving group represented by the general formula (19) with an aromatic amine derivative represented by the general formula (20) in an appropriate solvent or without a solvent, an aromatic carboxylic acid amide derivative having a nitro group represented by the general formula (21) can be prepared. In the process, a suitable base can also be used.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile and the like; and inert solvents such as 1, 3-dimethyl-2-imidazolidinone and the like.
- examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as di-potassium mono-hydrogen phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; and alkali metal alcoholates such as sodium methoxide, sodium ethoxide and the like.
- These bases may be suitably selected in the range of 0.01 to 5 mole equivalents, based on the compound represented by the general formula (19) and used accordingly.
- the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- an aromatic carboxylic acid halide derivative can be easily prepared from an aromatic carboxylic acid according to a usual method employing a halogenating agent.
- a halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride and the like.
- the compound represented by the general formula (21) can be prepared from the m-nitroaromatic carboxylic acid derivative and the compound represented by the general formula (20) without using a halogenating agent.
- a method thereof a method suitably using an additive such as 1-hydroxybenzotriazole or the like and employing a condensation agent using N,N'-dicyclohexylcarbodiimide according to a method as described, for example, in Chem. Ber. p. 788 (1970 ) can be exemplified.
- Other condensation agents to be used in this case include, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1,1'-carbonylbis-1H-imidazole and the like.
- the compound represented by the general formula (21) can be prepared according to a method as described in J. Am. Chem. Soc. p. 5012 (1967 ).
- chloroformate esters to be used in this case include isobutyl chloroformate, isopropyl chloroformate and the like.
- diethylacetyl chloride, trimethylacetyl chloride and the like can be cited.
- Both the method using a condensation agent and mixed anhydride procedure are not restricted to the solvent, reaction temperature and reaction time as described in the above literatures, and an inert solvent which does not remarkably hinder the suitable progress of the reaction may be used.
- the reaction temperature and reaction time may be suitably selected as the reaction proceeds.
- the former method can be carried out in a proper solvent in the presence of a catalyst, at ordinary pressure or under pressure, in a hydrogen atmosphere.
- a catalyst include, for example, palladium catalysts such as palladium carbon and the like, nickel catalysts such as Raney nickel and the like, cobalt catalysts, ruthenium catalysts, rhodium catalysts, platinum catalysts and the like.
- the solvent examples include, for example, water; alcohols such as methanol, ethanol and the like; aromatic hydrocarbons such as benzene, toluene and the like; chained ethers or cyclic ethers such as ether, dioxane, tetrahydrofuran and the like; and esters such as ethyl acetate and the like.
- the pressure may be suitably selected in the range of 0.1 to 10 MPa
- the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use
- the reaction time may be properly selected in the range of several minutes to 96 hours.
- the compound of the general formula (22) can be more effectively prepared.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile and the like; and inert solvents such as 1,3-dimethyl-2-imidazolidinone and the like.
- examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as di-potassium mono-hydrogen phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; and alkali metal alcoholates such as sodium methoxide, sodium ethoxide and the like.
- These bases may be suitably selected in the range of 0.01 to 5 mole equivalents based on the compound represented by the general formula (22) and used accordingly.
- the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours. Furthermore', a method employing a condensation agent and a mixed anhydride procedure as described in 1-(i) can also be used for the production thereof.
- the compound represented by the general formula (26) can also be prepared by a separate method comprising reacting an alkylating agent such as dimethyl sulfate, diethyl sulfate or the like, instead of the compound represented by the general formula (25) , with the compound represented by the general formula (24).
- an alkylating agent such as dimethyl sulfate, diethyl sulfate or the like
- a compound represented by the general formula (29) can be prepared by a known usual method comprising reacting a compound represented by the general formula (28) with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride or the like.
- a 1 , A 2 , A 3 , A 4 , G 1 , R 1 , R 2 , X, n, Q 1 , Q 2 and L are the same as those described above.
- a 1 , A 2 , A 3 , A 4 , R 1 , R 2 , X, n, Q 1 and Q 2 are the same as those described above.
- Compounds represented by the general formulae (35) and (36) can be prepared from a compound represented by the general formula (34) according to the conditions described in 3-(i). The conditions such as a solvent, reaction temperature and the like are not restricted to those described in the literatures. These two compounds can be easily separated and purified by a known separation and purification technique such as silica gel column chromatography and the like.
- a compound represented by the general formula (38) can be prepared by carrying out an amination reaction using ammonia according to the conditions described, for example, in J. Org. Chem. p. 280 (1958 ).
- the conditions such as a reaction solvent and the like are not restricted to those described in the literatures, and an inert solvent which does not remarkably hinder the proper progress of the reaction may be used.
- the reaction temperature and reaction time may be suitably selected as the reaction proceeds.
- examples of the amination agent include methylamine, ethylamine or the like, in addition to ammonia .
- R 2 represents the same as those described above; Y 1 and Y 5 independently represent a methyl group, a chlorine atom, a bromine atom or an iodine atom; Y 2 and Y 4 represent the same as those described above; R f represents a C1-C6 perfluoroalkyl group; and m represents 1 or 2.
- haloalkyl iodide represented by the general formula (41) examples include trifluoromethyl iodide, pentafluoroethyl iodide, heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide, nonafluoro-n-butyl iodide, nonafluoroisobutyl iodide and the like. These may be suitably used in the range of 1 to 10 mole equivalents, based on the compound represented by the general formula (40).
- the solvent to be used in the process is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction.
- examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile and the like; and inert solvents
- the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- halogenating agent examples include chlorine, bromine, iodine, N-chlorosuccinic acid imide, N-bromosuccinic acid imide, N-iodosuccinic acid imide and the like. These may be suitably used in the range of 1 to 10 mole equivalents, based on a compound represented by the general formula (42).
- an appropriate solvent can also be used, but a solvent in use is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction.
- a solvent in use is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction.
- examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichlbromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such
- the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- a compound represented by the general formula (44) can be prepared by using a suitable oxidant.
- a suitable oxidant include organic peroxides such as m-chloroperbenzoic acid and the like, sodium metaperiodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, dinitrogen tetraoxide, acyl nitrate, iodine, bromine, N-bromosuccinic acid imide, iodosylbenzyl, t-butyl hypochlorite and the like.
- the solvent to be used in this process is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction. These solvents can be used singly or in combination of 2 or more kinds. Particularly preferable is a polar solvent.
- the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- the compound of the present invention can be prepared by suitably selecting a preparation method as illustrated in the present invention using an aniline derivative represented by the general formula (43), (44), (43-2) or (44-2).
- R 2 , Y 1 , Y 2 , Y 4 , Y 5 , R f and m represent the same as those described in the preparation method 6.
- An aniline derivative represented by the general formula (47) can be prepared using a compound represented by the general formula (45) as a starting raw material according to the preparation method 6. Furthermore, by suitably selecting a preparation method as illustrated in the present invention, the compound of the present invention can be prepared.
- a 1 , A 2 , A 3 , A 4 , X, n, G 2 , R 2 and Q 2 represent the same as those above.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, buty
- the base examples include organic bases such as triethylamine, tributylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as potassium mono-hydrogen phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and the like; organolithiums such as n-butyl lithium and the like; and Grignard reagents such as ethyl magnesium bromide and the like.
- organic bases such as triethylamine, tributylamine, pyridine, 4-dimethylaminopyridine and the like
- alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like
- carbonates such as
- bases may be suitably selected in the range of 0.01 to 5 mole equivalents, based on the compound represented by the general formula (48) or may be used as a solvent.
- the reactant examples include halogenated alkyls such as methyl iodide, ethyl bromide, trifluoromethyl iodide, 2,2,2-trifluoroethyl iodide and the like; halogenated allyls such as allyl iodide and the like; halogenated propargyls such as propargyl bromide and the like; halogenated acyls such as acetyl chloride and the like; acid anhydrides such as trifluoroacetic anhydride and the like; and alkyl sulfuric acids such as dimethyl sulfate, diethyl sulfate and the like.
- halogenated alkyls such as methyl iodide, ethyl bromide, trifluoromethyl iodide, 2,2,2-trifluoroethyl iodide and the like
- halogenated allyls such as allyl io
- reactants may be suitably selected in the range of 1 to 5 mole equivalents, based on the compound represented by the general formula (48) or may be used as a solvent.
- the reaction temperature may be suitably selected in the range of -80 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, buty
- the catalyst examples include palladium catalysts such as palladium carbon, palladium hydroxide carbon and the like, nickel catalysts such as Raney nickel and the like, cobalt catalysts, platinum catalysts, ruthenium catalysts, rhodium catalysts and the like.
- aldehydes include formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde and the like.
- ketones include acetone, perfluoroacetone, methylethyl ketone and the like.
- the reaction pressure may be suitably selected in the range of 1 to 100 atm.
- the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, buty
- borohydrides such as sodium borohydride, sodium cyanoborohydride, sodium triacetate borohydride and the like.
- aldehydes include formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde and the like.
- ketones include acetone, perfluoroacetone, methylethyl ketone and the like.
- the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, buty
- Examples of the formylating agent include formic anhydrides such as formaldehyde, formic acid, fluoroformic acid, formyl (2, 2-dimethylpropionic acid) and the like; formic acid esters such as phenyl formate and the like; pentafluorobenzaldehyde, oxazole and the like.
- the reducing agent examples include inorganic acids such as sulfuric acid and the like; organic acids such as formic acid and the like; borohydrides such as sodium borohydride, sodium cyanoborohydride and the like; boronic acid, lithium aluminum hydride and the like.
- the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- R c ' represents a hydroxy group or -O-R d (R d represents the same as those described above); and in the general formula (52), R c " represents a chlorine atom, a bromine atom or an iodine atom.
- a chlorine compound (a bromine compound or an iodine compound) represented by the general formula (52) can be prepared.
- an appropriate additive can also be used.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols
- halogenating agent examples include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, Rydon reagents, sulfonyl halides such as methanesulfonyl chloride, p-toluenesulfonyl chloride, benzenesulfonyl chloride and the like, sulfonium halides, sulfonate esters, chlorine, bromine, iodine, hypohalite esters, N-halogenoamines, hydrogen chloride, hydrogen bromide, sodium bromide, potassium bromide, cyanuric chloride, 1,3-dichloro-1,2,4-triazole, titanium (IV) chloride, vanadium (IV) chloride, arsenic (III) chloride, N,N-diethyl-1
- the additive examples include metal salts such as zinc chloride, lithium bromide and the like; organic bases such as a phase transfer catalyst, hexamethylphosphoric triamide and the like; inorganic acids such as sulfuric acid and the like; N,N-dimethylformamide and the like.
- halogenating agents may be suitably selected in the range of 0.01 to 10 mole equivalents, based on the compound represented by the general formula (1) or may be used as a solvent.
- the reaction temperature may be suitably selected in the range of -80 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, buty
- fluorinating agent examples include 1,1,2,2-tetrafluoroethyldiethylamine, 2-chloro-1,1,2-trifluoroethyldiethylamine, trifluorodiphenylphosphorane, difluorotriphenylphosphorane, fluoroformate esters, sulfur tetrafluoride, potassium fluoride, potassium hydrogen fluoride, cesium fluoride, rubidium fluoride, sodium fluoride, lithium fluoride, antimony (III) fluoride, antimony (V) fluoride, zinc fluoride, cobalt fluoride, lead fluoride, copper fluoride, mercury (II) fluoride, silver fluoride, silver fluoroborate, thallium (I) fluoride, molybdenum (VI) fluoride, arsenic (III) fluoride, bromine fluoride, selenium (IV) fluoride, tris(dimethylamino)sulfonium difluoro
- These fluorinating agents can be used singly or in combination of 2 or more kinds. These halogenating agents may be suitably selected in the range of 1 to 10 mole equivalents, based on the compound represented by the general formula (53) or may be suitably used as a solvent.
- An additive may also be used and examples thereof include crown ethers such as 18-crown-6 and the like; phase transfer catalysts such as tetraphenylphosphonium salts and the like; inorganic salts such as calcium fluoride, calcium chloride and the like; metal oxides such as mercury oxide and the like; ion exchange resins and the like.
- crown ethers such as 18-crown-6 and the like
- phase transfer catalysts such as tetraphenylphosphonium salts and the like
- inorganic salts such as calcium fluoride, calcium chloride and the like
- metal oxides such as mercury oxide and the like
- ion exchange resins and the like ion exchange resins and the like.
- the reaction temperature may be suitably selected in the range of -80 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- a compound represented by the general formula (56) can be prepared from a compound represented by the general formula (55) according to the method described in the preparation method 10.
- a compound represented by the general formula (58) can be prepared from a compound represented by the general formula (57) according to the method described in the preparation method 11.
- a compound represented by the general formula (60) can be prepared from a compound represented by the general formula (59) according to the method described in the preparation method 10.
- desired products may be isolated according to a usual method from the reaction system after completion of the reaction, and can be purified, if needed, by carrying out operations such as recrystallization, column chromatography, distillation and the like. Furthermore, desired products can also be supplied to the next reaction process without isolating them from the reaction system.
- the compound represented by the general formula (2) can be prepared according to a method as described in International Publication No. 2005 / 21488 pamphlet.
- the compound represented by the general formula (3) can be prepared according to a method as described in International Publication No. 2003 / 8372 pamphlet.
- the compound represented by the general formula (4) can be prepared according to a method as described in International Publication No. 2005 / 42474 pamphlet.
- Typical compounds of the compound represented by the general formula (1) that is an active ingredient of an insecticide of the present invention are illustrated in Tables 1 to 5 below, but the present invention is not restricted thereto.
- n- refers to normal
- Me refers to a methyl group
- Et refers to an ethyl group
- n-Pr refers to a normal propyl group
- i-Pr refers to an isopropyl group
- n-Bu refers to a normal butyl group
- i-Bu refers to an isobutyl group
- s-Bu refers to a secondary butyl group
- t-Bu refers to a tertiary butyl group
- H refers to a hydrogen atom
- O refers to an oxygen atom
- S refers to a sulfur atom
- C refers to a carbon atom
- N refers to a nitrogen atom
- F refers to a fluorine atom
- Cl refers to a chlorine atom
- Br refers to a bromine atom
- I refers to an an an organic radical
- Tetramethylsilane is used as an internal standard substance to record shift values of 1 H-NMR as shown herein, unless otherwise particularly mentioned.
- 602 ⁇ 2.36 (6H, s), 2.56 (3H, s), 7.29-7.43 (7H, m), 7.55-7.57 (1H, m), 7.75-7.78 (1H, m), 7.84-7.88 (1H, m), 8.64-8.66 (1H, m).
- 607 ⁇ 2.34 (6H, s), 7.40 (1H, t, J 7.8Hz), 7.45 (2H, s), 7.57-7.62 (1H, m), 7.81-7.85 (1H, m), 8.22-8.25 (2H, m), 8.39-8.42 (2H, m), 10.12 (1H, s), 10.66 (1H, s).
- Typical compounds of the compound represented by the general formula (2) that is an active ingredient of the insecticide of the present invention are illustrated in Table 7 below, but the present invention is not restricted thereto.
- Typical compounds of the compound represented by the general formula (3) that is an active ingredient of the fungicide of the present invention are illustrated in Table 8 below, but the present invention is not restricted thereto.
- Me refers to a methyl group
- i-Pr refers to an isopropyl group
- t-Bu refers to a tertiary butyl group.
- Typical compounds of the compound represented by the general formula (4) that is an active ingredient of the fungicide of the present invention are illustrated in Table 9 below, but the present invention is not restricted thereto.
- Me refers to a methyl group
- i-Pr refers to an isopropyl group
- t-Bu refers to a tertiary butyl group.
- the insecticidal and fungicidal composition of the present invention exhibits excellent insecticidal and fungicidal effects and exerts an accurate control effect on harmful diseases and insect pests.
- insect pests there can be exemplified, for example, LEPIDOPTERA such as swift moth (Endoclyta excrescens), grape tree-borer (Endoclyta sinensis), swift moth (Palpifer sexnotata), strawberry tortrix moth (Acleris comariana), summer fruit tortrix moth (Adoxophyes orana fasciata), small tea tortrix moth (Adoxophyes sp.), Asiatic leaf roller (Archips breviplicanus), apple tortrix (Archips fuscocupreanus), brown oak tortrix (Archips xylosteanus), tortrix moth (Bactra furfurana), tobacco leaf worm (Cnephasia cinereipalpana), nut fruit tortrix (C
- rice blast (Pyricularia oryzae) can be cited.
- insecticidal and fungicidal composition of the present invention there can be exemplified, for example, application to the plant itself (foliar spraying), application to the nursery box (nursery box application), application to the soil (soil treatments such as soaking into soil, mixture into soil, side dressing, dispersion on soil or spraying on soil) , application of paddy water (submerged application or rice field application), application to the seed (seed treatment) and the like.
- the insecticidal and fungicidal composition of the present invention is generally prepared into conveniently usable forms according to an ordinary manner for preparation of agricultural and horticultural chemicals. That is, the composition may be blended with a suitable inert carrier, optically along with an adjuvant, in a proper proportion and prepared into a suitable preparation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust, tablets or the like through dissolution, separation, suspension, mixing, impregnation, adsorption or adhering.
- a suitable inert carrier optically along with an adjuvant
- the inert carrier which can be used in the present invention may be either solid or liquid.
- a material which can be an inert solid carrier includes, for example, soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residue of vegetables, synthetic polymers such as powdered synthetic resins, inorganic mineral powder such as lays (for example, kaolin, bentonite, acid clay and the like), talcs (for example, talc, pyrophyllite and the like), silica powders or flakes (for example, diatomaceous earth, silica sand, mica, white carbon [synthetic, high-dispersion silicic acid, also called finely divided hydrated silicon, hydrated silicic acid, some of commercially available products contain calcium silicate as the major component]), activated carbon, powdered sulfur, pumice stone, calcined diatomite, brick groats, fly ash,
- a material which can be the inert liquid carrier is selected from such a material which itself has solvency or which does not have such solvency but is capable of dispersing an effective ingredient compound with the aid of an adjuvant.
- the following are typical examples of the carrier and can be used singly or in combination of two or more kinds.
- Examples thereof include water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol and the like), ketones (for example, acetone, methylethyl ketone, methylisobutyl ketone, diisobutyl ketone, cyclohexanone and the like), ethers (for example, ethyl ether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran and the like), aliphatic hydrocarbons (for example, kerosene, mineral oil and the like), aromatic hydrocarbons (for example, benzene, toluene, xylene, solvent naphtha, alkyl naphthalene and the like), halogenated hydrocarbons (for example, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene and the like), esters (for example, ethyl
- adjuvant As an adjuvant, typical adjuvants mentioned below can be exemplified. These adjuvants can be used depending on purposes and used singly or in combination of two or more kinds or cannot be used at all in some cases.
- a surfactant is used.
- surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonates, lignin sulfonates, higher alcohol sulfate esters and the like.
- the following adjuvants can be used.
- examples thereof include casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum Arabic, polyvinyl alcohols, pine oil, bran oil, bentonite, Xanthan gum, lignin sulfonates and the like.
- adjuvants such as waxes, stearates, alkyl phosphates and the like can be used.
- adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for suspendible products.
- adjuvants such as silicon oils can also be used.
- the insecticidal and fungicidal composition of the present invention is stable to light, heat, oxidation and the like.
- an anti-oxidant or an ultraviolet absorber for example, a phenol derivative such as BHT (2,6-di-t-butyl-4-methylphenol) and BHA (butylated hydroxyanisole), a bisphenol derivative or arylamines such as phenyl- ⁇ -naphthylamine, phenyl- ⁇ -naphthylamine, condensates of phenetidine and acetone, or a stabilizer such as a benzophenone-based compound is added in a proper amount when necessary, whereby it is possible to obtain a composition with much stabilized effect.
- a phenol derivative such as BHT (2,6-di-t-butyl-4-methylphenol) and BHA (butylated hydroxyanisole)
- a bisphenol derivative or arylamines such as phenyl- ⁇ -naphth
- the weight ratio of the active compound in the present invention can be varied in a relatively wide range.
- the fungicidal active compound represented by the general formula (3) or (4) is contained from 0.02 to 50 weight parts and preferably from 0.1 to 20 weight parts per 1 weight part of the insecticidal active compound represented by the general formula (1) or (2).
- the content of the active ingredient of the insecticidal and fungicidal composition of the present invention is usually from 0.1 weight % to 20 weight % for dust formulation, from 5 weight % to 50 weight % for emulsifiable concentrate, from 10 weight % to 90 weight % for wettable powder, from 0.1 weight % to 20 weight % for granule, and from 10 weight % to 90 weight % for flowable formulation.
- the amount of the carrier in each formulation is usually from 60 weight % to 99 weight % for dust formulation, from 40 weight % to 95 weight % for emulsifiable concentrate, from 10 weight % to 90 weight % for wettable powder, from 80 weight % to 99 weight % for granule, and from 10 weight % to 90 weight % for flowable formulation.
- the amount of the adjuvant is usually from 0.1 weight % to 20 weight % for dust formulation, from 1 weight % to 20 weight % for emulsifiable concentrate, from 0.1 weight % to 20 weight % for wettable powder, from 0.1 weight % to 20 weight % for granule, and from 0.1 weight % to 20 weight % for flowable formulation.
- the insecticidal and fungicidal composition of the present invention may be applied to crops which are expected to create diseases and insect pests or places where such creation is not desired in an amount effective in controlling diseases and insect pests as intact, as appropriately diluted with water or the like, or as suspended, and used accordingly.
- the amount thereof is varied according to various factors such as purpose, target diseases and insect pests, reared status of crops, occurrence trend of diseases and insect pests, weather, environmental conditions, the type of formulation, method of application, place of application, time of application and the like.
- the active ingredient is preferably used at a concentration of from 0.0001 to 5000 ppm and preferably from 0.01 to 1000 ppm.
- the amount of the composition applied per 10 a is generally from 1 to 500 g as the active ingredient.
- the insecticidal and fungicidal composition of the present invention may be used singly for preventing various diseases and insect pests which are injurious to paddy rice, fruit trees, vegetables, other crops, flowers and the like. Also, it may be used in combination of one or more kinds of other insecticides and/or fungicides in order to obtain an excellent control effect.
- insecticidal and fungicidal composition of the present invention When used in combination with one or more kinds of other insecticides and/or fungicides, the insecticidal and fungicidal composition of the present invention may be used as a mixed solution with other insecticides and/or fungicides, or the insecticidal and fungicidal composition of the present invention may be used as a mixture with other insecticides and/or fungicides at the time of application of the agrochemicals.
- insecticidal and fungicidal composition of the present invention can be used as a mixture with a plant protection agent such as a herbicide, a fertilizer, a soil conditioner, a plant growth regulator and the like or a material, whereby a multi-purpose composition with an excellent effect can be prepared.
- a plant protection agent such as a herbicide, a fertilizer, a soil conditioner, a plant growth regulator and the like or a material, whereby a multi-purpose composition with an excellent effect can be prepared.
- a desired title product was prepared according to the conditions as described in Example 1-3 as a white solid.
- a desired title product was prepared from N-methyl-2-bromo-4-heptafluoroisopropyl-6-methylaniline according to the conditions as described in Example 1 as a white solid.
- a desired title product was prepared from N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzthioamide according to the conditions as described in Example 1-3.
- a mixed solution of 2.20 g of 2,6-dibromo-4-heptafluoroisopropylaniline, 1.46 g of 3-nitrobenzoyl chloride and 10 ml of pyridine was stirred at 70 degree centigrade for 20 hours.
- the resulting solution was returned to room temperature, and then ethyl acetate and IN hydrochloric acid were added thereto.
- An organic layer was separated and then washed with saturated baking soda solution.
- the solvent was removed under a reduced pressure and the resulting residue was dissolved in a mixed solvent of 8 ml of tetrahydrofuran and 2 ml of methanol.
- reaction solution was cooled down to 5 degree centigrade, 0.30 g of sodium hydroxide was added thereto, the mixture was stirred for 2 hours, and then ethyl acetate and water were added thereto.
- An organic layer was separated and washed with saturated baking soda solution, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with hexane to obtain 2.19 g of the desired product (Yield: 73%) as a light brown solid.
- part(s) refers to weight part(s).
- insecticidal and fungicidal composition of the present invention has excellent insecticidal and fungicidal activities
- the following test examples are illustrated. However, the present invention is not restricted to these test examples.
- Rice (cultivar: koshihikari) cultured in a nursery box was treated with a granule formulation of a prescribed amount, and then 4 seedlings thereof planted in a 1/5000a pot were transplanted to 8 pots. After 14 days from the treatment, canopies in 4 pots were cut and put into a plastic cup (diameter: 10 cm, height: 10 cm) along with 10 two-year-old larvae of Chilo suppressalis. After 4 days, the mortality was examined (4 replications).
- a granule formulation of a prescribed amount was used in a submerged application for 4 pots of 1/5000a rice (cultivar: koshihikari; 4 leaf stage) pots. After 7 days from the treatment, canopies in 2 pots were cut and put into a plastic cup (diameter: 10 cm, height: 10 cm) along with 10 two-year-old larvae of Chilo suppressalis. After 4 days, the mortality was examined (2 replications). Furthermore, after 14 days from the treatment, the other 2 pots were put into an artificial weather chamber (set condition: 25 degree centigrade, 12-12 hr light-dark cycle), and a spore suspension of Pyricularia oryzae was spray-inoculated.
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Abstract
Description
- The present invention relates to a novel insecticidal and fungicidal composition exhibiting excellent insecticidal and fungicidal actions for the labor-saving control of crop diseases and insect pests.
- The compound represented by the general formula (1) of the present invention is a novel compound having an insecticidal activity.
- In International Publication No.
2000 / 55120 pamphlet andUS Patent No. 6548514 , a compound similar to the compound represented by the general formula (1) of the present invention for medical use is described. But activity against insects is never described therein. Furthermore, it is obvious that such compounds are not included in the claims of the present invention. - In International Publication No.
2000 / 7980 - In
US Patent Laid-Open No. 2002-032238 , a compound similar to the compound represented by the general formula (1) of the present invention for medical use is described. But activity against insects is never described therein. Furthermore, it is obvious that such a compound is not included in the claims of the present invention. - Meanwhile, the compound represented by the general formula (2) is described in International Publication No.
2005 / 21488 pamphlet before the application of the present invention and the compound itself has an insecticidal action. In addition, in International Publication No.2003 / 008372 pamphlet and International Publication No.2005 / 042474 pamphlet, it has been described that the compound represented by the general formula (3) or (4) has a control action against rice blast (Pyricularia oryzae) - However, these active compounds have an action exhibiting any of an insecticidal effect or a fungicidal effect with the use of a single agent thereof, but cannot control crop diseases and insect pests at the same time.
- Patent Document 1: International Publication No.
2000 / 55120 pamphlet
Patent Document 2:US Patent No. 6548514
Patent Document 3: International Publication No.2000 / 7980
Patent Document 4:US Patent Laid-Open No. 2002-032238
Patent Document 5: International Publication No.2005 / 21488 pamphlet
Patent Document 6: International Publication No.2003 / 8372
Patent Document 7: International Publication No.2005 / 42474 pamphlet - The present invention is to provide an insecticidal and fungicidal composition capable of controlling crop diseases and insect pests at the same time by combining an insecticidal active ingredient and a fungicidal active ingredient.
- In order to solve the aforementioned object, the present inventors have repeatedly conducted an extensive study and as a result, have found that an insecticidal and fungicidal composition containing one or more compounds represented by the general formula (1) or (2) as insecticidal active ingredients, and one or more compounds represented by the general formula (3) or (4) as fungicidal active ingredients has excellent insecticidal and fungicidal effects on crop diseases and insect pests. Thus, the present invention has been completed.
- That is, the present invention is specified by the following matters:
- [1] an insecticidal and fungicidal composition comprising; one or two or more compounds selected from compounds represented by the general formula (1) or (2); and one or two or more compounds selected from compounds represented by the general formula (3) or (4) as active ingredients,
-
- wherein, in the formula (1), X1 is a hydrogen atom or a fluorine atom; R1 and R2 are independently a hydrogen atom or a C1-C4 alkyl group; Q1 is a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group,
a pyridyl group, or
a pyridyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; and
Q2 is represented by the general formula (A), -
- wherein, in the formula (A), Y1 and Y5 may be the same or different and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C2-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group, or
-
- wherein, in the formula (2), X2 is a hydrogen atom or a fluorine atom; R4 and R5 are independently a hydrogen atom or a C1-C4 alkyl group; R3 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group,
- -E1-Z1-R6 (wherein, in the formula, E1 represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group or a C3-C4 haloalkynylene group; R6 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group or a C2-C6 haloalkynyl group; Z1 represents -O-, -S-, -SO-, -SO2-, -C(=O)-, -C(=O)O-, -OC(=O)-, -N(R7)-, -C(=O)N(R7)- or -N(R7)C(=O)- (R7 represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group or a C1-C4 alkoxycarbonyl group)) or
- -E2-R8 (wherein, in the formula, E2 represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group or a C3-C4 haloalkynylene group; R8 represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group and a C1-C4 alkoxycarbonyl group,
a pyridyl group,
a substituted pyridyl group having one or more substituents selected from a halogen atom, a C1-C6 haloalkyl group and a C1-C6 haloalkoxy group,
a thienyl group, or
a tetrahydrofuran group); and
Q3 represents the general formula (B), -
- wherein, in the formula (B), Y6 and Y10 may be the same or different and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 and Y9 represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group, and
-
- wherein, in the formula (3) , R11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group or a heterocyclic alkyl group; R12 and R17 independently represent a hydrogen atom; R13 and R14 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R15 and R16 independently represent a hydrogen atom; and R18 represents an aryl group or a heterocycle, or
-
- wherein, in the formula (4), R21 represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen or an alkenyl group having 2 to 6 carbon atoms substituted with halogen; R22 and R27 independently represent a hydrogen atom; R23 and R24 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R25 and R26 independently represent a hydrogen atom; and R28 represents an aryl group or a heterocycle;
- [2] an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (1) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (3) as set forth in [1] as active ingredients;
- [3] an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (1) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (4) as set forth in [1] as active ingredients;
- [4] an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (2) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (3) as set forth in [1] as active ingredients; and
- [5] an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (2) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (4) as set forth in [1] as active ingredients.
- The nursery box treatment of paddy rice using the insecticidal and fungicidal composition of the present invention is helpful in decreasing the amount of a liquid chemical per unit area and reducing the influence on the environment as well as in reducing burden of a farmhouse's labor. Furthermore, it is further helpful in saving much labor by mixing with a fertilizer and carrying out fertilizer application at the time of rice transplantation or setting. Accordingly, the insecticidal and fungicidal composition of the present invention is extremely effective in control of diseases and insect pests at the same time, and saving labor for agricultural products, and horticultural products, and provides technical inventiveness which is also excellent in industrial effectiveness.
- Control of insect pests and control of diseases must be conducted with the use of a single active compound, but the insecticidal and fungicidal composition of the present invention is capable of the labor-saving control of diseases and insect pests at the same time.
- The present invention will be described in more detail below. Wordings used in general formulae (1) and the (2) of the present invention have the respective meanings as described hereinafter in terms of definitions.
- The "halogen atom" represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
- In expression of "Ca-Cb (a and b represent an integer of not less than 1)", for example, "C1-C3" refers to 1 to 3 carbon atoms, "C2-C6" refers to 2 to 6 carbon atoms, and "C1-C4" refers to 1 to 4 carbon atoms.
- "n-" refers to normal, "i-" refers to iso, "s-" refers to secondary and "t-" refers to tertiary.
- The "C1-C3 alkyl group" represents, for example, linear, branched or cyclic alkyl groups having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, cyclopropyl and the like. The "C1-C4 alkyl group" represents, for example, linear or branched alkyl groups having 1 to 4 carbon atoms such as n-butyl, s-butyl, i-butyl, t-butyl and the like, in addition to "C1-C3 alkyl group." The "C1-C6 alkyl group" represents, for example, linear or branched alkyl groups having 1 to 6 carbon atoms such as n-pentyl, 2-pentyl, 3-pentyl, neopentyl, n-hexyl, 2-hexyl, 4-methyl-2-pentyl, 3-methyl-n-pentyl and the like, in addition to "C1-C4 alkyl group."
- The "C1-C3 haloalkyl group" represents, for example, linear or branched alkyl groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2-dibromoethyl, 2,2,2-tribromoethyl, 2-iodoethyl, pentafluoroethyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo-n-propyl, 1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl, 1,1,1-trifluoro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, heptafluoro-i-propyl, heptafluoro-n-propyl and the like. The "C1-C4 haloalkyl group" represents, for example, linear or branched alkyl groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 4-fluoro-n-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl and the like, in addition to "C1-C3 haloalkyl group." The "C1-C6 haloalkyl group" represents, for example, linear or branched alkyl groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
- The "C2-C4 alkenyl group" represents, for example, alkenyl groups of 2 to 4 carbon atoms having a double bond in the carbon chain such as vinyl, allyl, 2-butenyl, 3-butenyl and the like, and the "C2-C6 alkenyl group" represents, for example, alkenyl groups of 2 to 6 carbon atoms having a double bond in the carbon chain. The "C2-C4 haloalkenyl group" represents, for example, linear or branched alkenyl groups of 2 to 4 carbon atoms having a double bond in the carbon atom substituted with one or more halogen atoms which may be the same or different, such as 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4,4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl and the like, and the "C2-C6 haloalkenyl group" represents, for example, linear or branched alkenyl groups of 2 to 6 carbon atoms having a double bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.
- The "C2-C4 alkynyl group" represents, for example, linear or branched alkynyl groups of 2 to 4 carbon atoms having a triple bond in the carbon chain such as propargyl, 1-butyne-3-yl, 1-butyne-3-methyl-3-yl and the like, and the "C2-C6 alkynyl group" represents, for example, linear or branched alkynyl groups of 2 to 6 carbon atoms having a triple bond in the carbon chain. The "C2-C4 haloalkynyl group" represents, for example, linear or branched alkenyl groups of 2 to 4 carbon atoms having a triple bond in the carbon chain substituted with one or more halogen atoms which may be the same or different, the "C2-C6 haloalkynyl group" represents, for example, linear or branched alkenyl groups of 2 to 6 carbon atoms having a triple bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.
- The "C3-C6 cycloalkyl group" represents, for example, cycloalkyl groups of 3 to 6 carbon atoms having a cyclic structure, such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl and the like, and the "C3-C8 cycloalkyl group" represents, for example, cycloalkyl groups of 3 to 8 carbon atoms having a cyclic structure. The "C3-C6 halocycloalkyl group" represents, for example, cycloalkyl groups of 3 to 6 carbon atoms having a cyclic structure substituted with one or more halogen atoms which may be the same or different, such as 2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, 4-chlorocyclohexyl and the like, and the "C3-C8 halocycloalkyl group" represents, for example, cycloalkyl groups of 3 to 8 carbon atoms having a cyclic structure substituted with one or more halogen atoms which may be the same or different.
- The "C1-C3 alkoxy group" represents, for example, linear or branched alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy and the like, and the "C1-C6 alkoxy group" represents linear or branched alkoxy groups having 1 to 6 carbon atoms. The "C1-C3 haloalkoxy group" represents, for example, linear or branched haloalkoxy groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 3-fluoro-n-propyloxy and the like, the "C1-C4 haloalkoxy group" represents, for example, linear or branched haloalkoxy groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 1,1,1,3,3,4,4,4-octafluoro-2-butyloxy and the like, in addition to "C1-C3 haloalkoxy group," and the "C1-C6 haloalkoxy group" represents, for example, linear or branched haloalkoxy groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
- The "C1-C3 alkylthio group" represents, for example, linear, branched or cyclic alkylthio groups having 1 to 3 carbon atoms such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio and the like, the "C1-C4 alkylthio group" represents, for example, linear, branched or cyclic alkylthio groups having 1 to 4 carbon atoms such as n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio and the like, in addition to "C1-C3 alkylthio group," and the "C1-C6 alkylthio group" represents, for example, linear or branched alkylthio groups having 1 to 6 carbon atoms. The "C1-C3 haloalkylthio group" represents, for example, linear or branched alkylthio groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio and the like. The "C1-C4 haloalkylthio group" represents, for example, linear or branched alkylthio groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as nonafluoro-n-butylthio, nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio and the like, in addition to "C1-C3 haloalkylthio group," and the "C1-C6 haloalkylthio group" represents, for example, linear or branched alkylthio groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
- The "C1-C3 alkylsulfinyl group" represents, for example, linear, branched or cyclic alkylsulfinyl groups having 1 to 3 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl and the like, and the "C1-C6 alkylsulfinyl group" represents linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms. The "C1-C3 haloalkylsulfinyl group" represents, for example, linear or branched alkylsulfinyl groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl', heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl and the like, and the "C1-C6 haloalkylsulfinyl group" represents, for example, linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
- The "C1-C3 alkylsulfonyl group" represents, for example, linear, branched or cyclic alkylsulfonyl groups having 1 to 3 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl and the like, and the "C1-C6 alkylsulfonyl group" represents linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms. The "C1-C3 haloalkylsulfonyl group" represents, for example, linear or branched alkylsulfonyl groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl and the like, and the "C1-C6 haloalkylsulfonyl group" represents, for example, linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
- The "C1-C4 alkylamino group" represents, for example, linear, branched or cyclic alkylamino groups having 1 to 4 carbon atoms, such as methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, cyclopropylamino and the like, and the "di C1-C4 alkylamino group" represents, for example, linear or branched amino groups substituted with two alkyl groups having 1 to 4 carbon atoms which may be the same or different, such as dimethylamino, diethylamino, N-ethyl-N-methylamino and the like.
- The "C1-C4 alkylcarbonyl group" represents, for example, linear, branched or cyclic alkylcarbonyl groups having 1 to 4 carbon atoms, such as formyl, acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl and the like.
- The "C1-C4 haloalkylcarbonyl group" include linear or branched alkylcarbonyl groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, iodoacetyl, 3,3,3-trifluoropropionyl, 2,2,3,3,3-pentafluoropropionyl and the like.
- The "C1-C4 alkylcarbonyloxy group" represents, for example, linear or branched alkylcarbonyloxy groups having 1 to 4 carbon atoms, such as acetoxy, propionyloxy and the like.
- The "C1-C4 alkoxycarbonyl group" represents, for example, linear or branched alkoxycarbonyl groups having 1 to 4 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl and the like.
- The "C1-C4 perfluoroalkyl group" represents, for example, linear or branched alkyl groups having 1 to 4 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl and the like, and the "C2-C6 perfluoroalkyl group" represents, for example, linear or branched alkyl groups having 2 to 6 carbon atoms which are all substituted with fluorine atoms, such as pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl, perfluoro-n-pentyl, perfluoro-n-hexyl and the like.
- The "C1-C6 perfluoroalkylthio group" represents, for example, linear or branched alkylthio groups having 1 to 6 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethylthio, pentafluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio, nonafluoro-i-butylthio, perfluoro-n-pentylthio, perfluoro-n-hexylthio and the like.
- The "C1-C6 perfluoroalkylsulfinyl group" represents, for example, linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2-butylsulfinyl, nonafluoro-i-butylsulfinyl, perfluoro-n-pentylsulfinyl, perfluoro-n-hexylsulfinyl and the like.
- The "C1-C6 perfluoroalkylsulfonyl group" represents, for example, linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, nonafluoro-2-butylsulfonyl, nonafluoro-i-butylsulfonyl, perfluoro-n-pentylsulfonyl, perfluoro-n-hexylsulfonyl and the like.
- The "C1-C4 alkylene group" represents, for example, linear or branched alkylene groups having 1 to 4 carbon atoms such as methylene, ethylene, propylene, dimethylmethylene, isobutylene and the like. The "C2-C4 alkenylene group" represents, for example, linear or branched alkenylene groups of 2 to 4 carbon atoms having a double bond in the carbon atom. The "C3-C4 alkynylene group" represents, for example, linear or branched alkynylene groups of 3 to 4 carbon atoms having a triple bond in the carbon chain. The "C1-C4 haloalkylene group" represents, for example, linear or branched alkylene groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as chloromethylene, chloroethylene, dichloromethylene, difluoromethylene and the like. The "C2-C4 haloalkenylene group" represents, for example, linear or branched alkynylene groups of 2 to 4 carbon atoms having a double bond in the carbon chain substituted with one or more halogen atoms which may be the same or different. The "C3-C4 haloalkynylene group" represents, for example, linear or branched alkynylene groups of 3 to 4 carbon atoms having a triple bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.
- The compounds represented by the general formulae (1) and (2) of the present invention contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula in some cases and have two or more optical isomers in some cases. However, the present invention also includes all of the respective optical isomers and mixtures consisting of these isomers in any ratio. Furthermore, the compounds represented by the general formulae (1) and (2) of the present invention have two or more geometrical isomers derived from a carbon-carbon double bond in its structural formula in some cases. However, the present invention also includes all of the respective geometrical isomers and mixtures consisting of these isomers in any ratio.
- As the substituents in the compounds represented by the general formulae (1) and (2) of the present invention, preferable substituents or atoms are as follows.
- R1 is preferably a hydrogen atom or a C1-C4 alkyl group and further preferably a hydrogen atom, a methyl group or an ethyl group.
- R2 is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- R4 is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- R5 is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- X1 is preferably a hydrogen atom or a fluorine atom.
- X2 is preferably a hydrogen atom or a fluorine atom.
- Q1 is preferably a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an acetylamino group,
a pyridyl group, or
a pyridyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an acetylamino group,
and further preferably a phenyl group,
a substituted phenyl group having one to three substituents which may be the same or different and are selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group,
a pyridyl group, or
a pyridyl group having one to two substituents which may be the same or different and are selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group. - Q2 is preferably is a substituted phenyl group represented by the general formula (A). In the formula, Y1 and Y5 are preferably independently a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group or a cyano group; Y2 and Y4 are preferably a hydrogen atom, a halogen atom or a methyl group, and further preferably a hydrogen atom; and Y3 is preferably a pentafluoroethyl group, a heptafluoro-n-propyl group, a heptafluoro-i-propyl group, a nonafluoro-n-butyl group, a nonafluoro-2-butyl group, a nonafluoro-i-butyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro-n-propylthio group, a heptafluoro-i-propylthio group, a nonafluoro-n-butylthio group, a nonafluoro-2-butylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro-i-propylsulfinyl group, a nonafluoro-n-butylsulfinyl group, a nonafluoro-2-butylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptafluoro-i-propylsulfonyl group, a nonafluoro-n-butylsulfonyl group or a nonafluoro-2-butylsulfonyl group. Q3 is preferably a substituted phenyl group represented by the general formula (B). In the formula, Y6 and Y10 are preferably independently a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group or a cyano group; Y7 and Y9 are preferably a hydrogen atom, a halogen atom or a methyl group, and further preferably a hydrogen atom; Y8 is preferably a pentafluoroethyl group, a heptafluoro-n-propyl group, a heptafluoro-i-propyl group, a nonafluoro-n-butyl group, a nonafluoro-2-butyl group, a nonafluoro-i-butyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro-n-propylthio group, a heptafluoro-i-propylthio group, a nonafluoro-n-butylthio group, a nonafluoro-2-butylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro-i-propylsulfinyl group, a nonafluoro-n-butylsulfinyl group, a nonafluoro-2-butylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptafluoro-i-propylsulfonyl group, a nonafluoro-n-butylsulfonyl group or a nonafluoro-2-butylsulfonyl group; R3 is preferably a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, -E1-Z1-R6 (wherein, in the formula, E1 represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group or a C3-C4 haloalkynylene group; R6 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group or a C2-C6 haloalkynyl group; and Z1 represents -O-, -S-, -SO- or -SO2-), -E2-R8 (wherein, in the formula, E2 represents a C1-C4 alkyl group, a C2-C4 alkenyl group, a C3-C4 alkynyl group, a C1-C4 haloalkyl group, a C2-C4 haloalkenyl group or a C3-C4 haloalkynyl group; and R8 represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group and a C1-C4 alkoxycarbonyl group,
a pyridyl group, or
a substituted pyridyl group having one or more substituents selected from a halogen atom, a C1-C6 haloalkyl group and a C1-C6 haloalkoxy group); and R3 is more preferably a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, -E1-Z1-R6 (wherein, in the formula, E1 represents a C1-C4 alkylene group or a C1-C4 haloalkylene group; R6 represents a C1-C6 alkyl group; and Z1 represents -O-, -S-, -SO-, -SO2-), or -E2-R8 (wherein, in the formula, E2 represents a C1-C4 alkyl group; and R8 represents a C3-C8 cycloalkyl group, a cyano group,
a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, a cyano group and a nitro group,
a pyridyl group,
a substituted pyridyl group having one or more substituents selected from a halogen atom, a C1-C6 haloalkyl group and a C1-C6 haloalkoxy group,
a thienyl group, or
a tetrahydrofuran group). - In the compounds represented by the general formulae (3) and (4), typical examples of the substituent can be cited as follows, but the present invention is not restricted to the following substituents.
- Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and the like.
- Examples of the alkenyl group having 2 to 6 carbon atoms include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group and the like.
- Examples of the alkyl group having 1 to 6 carbons substituted with halogen include chlorine substituted alkyl groups such as a chloromethyl group, a 2-chloroethyl group, a 2,2,2-trichloroethyl group, a 3-chloro-1-propyl group, a 4-chloro-1-butyl group and the like; fluorine substituted alkyl groups such as a 2-fluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,1,3,3,3-hexafluoro-2-propyl group, a 1,3-difluoro-2-propyl group, a 5-fluoro-1-pentyl group, a 6,6,6,5,5,4,4,3,3-nonafluoro-1-hexyl group, a 1-ethoxy-2,2,2-trifluoroethyl group and the like; bromine substituted alkyl groups such as a 2-bromoethyl group., a 1,3-dibromo-2-propyl group and the like; iodine substituted alkyl groups such as a 2-iodoethyl group and the like; and alkyl groups containing two or more halogens such as a 3-bromo-1,1,1-trifluoro-2-propyl group and the like.
- Examples of the cycloalkyl group having 3 to 6 carbons substituted with halogen include chlorine substituted cycloalkyl groups such as a chlorocyclopropyl group, a 2-chlorocyclobutyl group, a 2-chlorocyclopentyl group, a 2-chlorocyclohexyl group, a 3-chlorocyclohexyl group, a 4-chlorocyclohexyl group and the like; fluorine substituted cycloalkyl groups such as a 2-fluorocyclohexyl group, a 2,2,3,3-tetrafluorocyclopropyl group and the like; bromine substituted cycloalkyl groups such as a 2-bromocyclohexyl group and the like; and iodine substituted cycloalkyl groups such as a 2-iodocyclohexyl group and the like.
- Examples of the alkenyl group having 2 to 6 carbons substituted with halogen include chlorine substituted alkenyl group such as a 2-chloro-2-propenyl group, a 5-chloro-4-pentenyl group and the like; and fluorine substituted alkenyl groups such as a 4,4,4-trifluoro-2-butenyl group, a 6,6,6-trifluoro-5-hexenyl and the like.
- Examples of the aryl group include a phenyl group, a naphthyl group and the like.
- Examples of the heterocycle include a pyridyl group, a pyrimidyl group, a thienyl group, a furanyl group, a pyrazolyl group, an imidazolyl group, an isothiazolyl group, an isoxazolyl group, an indolyl group, a quinolyl group, a benzofuranyl group, a benzothienyl group, a benzoxazolyl group, a benzoisoxazolyl group, a benzimidazoly group, a benzothiazolyl group, a benzoisothiazolyl group and the like.
- As the substituents of the aryl group and the heterocycle, there can be respectively exemplified, for example, alkyl groups such as a.methyl group, an ethyl group, a propyl group, a butyl group and the like; cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like; halogen substituted alkyl groups such as a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group, a trifluoroethyl group and the like; alkoxy groups such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like; halogen substituted alkoxy groups such as a trifluoromethoxy group, a difluoromethoxy group, a trifluoroethoxy group and the like; alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group and the like; aryloxycarbonyl groups such as a phenoxycarbonyl group and the like; alkylamino groups such as a methylamino group, an ethylamino group, a propylamino group, a butylamino group, a dimethylamino group and the like; cycloalkylamino groups such as a cyclopropylamino group, a cyclobutylamino group, a cyclopentylamino group, a cyclohexylamino group, a dicyclopropylamino group and the like; alkylcarbamoyl groups such as a methylcarbamoyl group, an ethylcarbamoyl group, a propylcarbamoyl group, a butylcarbamoyl group, a dimethylcarbamoyl group and the like; cycloalkylcarbamoyl groups such as a cyclopropylcarbamoyl group, a cyclobutylcarbamoyl group, a cyclopentylcarbamoyl group, a cyclohexylcarbamoyl group, a dicyclopropylcarbamoyl group and the like; alkylcarbonylamino groups such as a methylcarbonylamino group, an ethylcarbonylamino group, a propylcarbonylamino group, a butylcarbonylamino group and the like; cycloalkylcarbonylamino groups such as a cyclopropylcarbonylamino group, a cyclobutylcarbonylamino group, a cyclopentylcarbonylamino group, a cyclohexylcarbonylamino group and the like; alkyloxycarbonylamino groups such as a methyloxycarbonylamino group, an ethyloxycarbonylamino group, a propyloxycarbonylamino group, a butyloxycarbonylamino group and the like; cycloalkyloxycarbonylamino groups such as a cyclopropyloxycarbonylamino group, a cyclobutyloxycarbonylamino group, a cyclopentyloxycarbonylamino group, a cyclohexyloxycarbonylamino group and the like; alkylthio groups such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group and the like; halogen substituted alkylthio groups such as a trifluoromethylthio group, a difluoromethylthio group, a trifluoroethylthio group and the like; alkylsulfinyl groups such as a methanesulfinyl group, an ethanesulfinyl group, a propanesulfinyl group, a butanesulfinyl group and the like; halogen substituted alkylsulfinyl groups such as a trifluoromethanesulfinyl group, a difluoromethanesulfinyl group, a trifluoroethanesulfinyl group and the like; alkylsulfonyl groups such as a methanesulfonyl group, an ethanesulfonyl group, a propanesulfonyl group, a butanesulfonyl group and the like; halogen substituted alkylsulfonyl groups such as a trifluoromethanesulfonyl group, a difluoromethanesulfonyl group, a trifluoroethanesulfonyl group and the like; alkylsulfonamide groups such as a methanesulfonamide group, an ethanesulfonamide group, a propanesulfonamide group, a butanesulfonamide group and the like; halogen substituted alkylsulfonamide groups such as a trifluoromethanesulfonamide group, a difluoromethanesulfonamide group, a trifluoroethanesulfonamide group and the like; halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; and acyl groups such as an acetyl group, a benzoyl group and the like.
Typical preparation methods of the compound represented by the general formula (1) are illustrated below and the compound represented by the general formula (1) can be prepared according to the preparation methods, but the preparation method paths are not restricted to the following preparation methods. Preferable substituents or atoms in the compounds represented by the general formulae shown in the following preparation methods are illustrated below. - L is preferably a chlorine atom, a bromine atom or a hydroxy group.
- R1a is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- R2a is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.
- G1a and G2a are preferably independently an oxygen atom or a sulfur atom, and further preferably both of G1a and G2a are oxygen atoms.
- X1a is preferably a hydrogen atom or a halogen atom, and further preferably a hydrogen atom or a fluorine atom.
- X2a is preferably a hydrogen atom or a fluorine atom, and further preferably a hydrogen atom.
- X3a and X4a are preferably a hydrogen atom.
- Y1a and Y5a are preferably independently a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group or a cyano group.
- Y2a and Y4a are preferably a hydrogen atom, a halogen atom or a methyl group, and further preferably a hydrogen atom.
- Q1a is preferably a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an acetylamino group,
a pyridyl group, or
a pyridyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an acetylamino group,
and further preferably a phenyl group,
a substituted phenyl group having one to three substituents which may be the same or different and are selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group,
a pyridyl group, or
a pyridyl group having one to two substituents which may be the same or different and are selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group. - Ra and Rb are preferably independently a fluorine atom, a trifluoromethyl group, a pentafluoroethyl group or a heptafluoro-n-propyl group, and further preferably independently a fluorine atom, a trifluoromethyl group or a pentafluoroethyl group.
- Rc is preferably a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, an ethoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group, a p-toluenesulfonyloxy group, an acetoxy group or a trifluoroacetoxy group, and further preferably a hydroxy group, a chlorine atom, a bromine atom, a methoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group or a p-toluenesulfonyloxy group, and further preferably a hydroxy group, a chlorine atom or a bromine atom.
- Rc' is preferably a hydroxy group.
- Rc" is preferably a chlorine atom or a bromine atom.
- In the general formulae shown in the following preparation methods, X1, X2, X3, X4, Y1, Y2, Y4, Y5, G1, G2, R1, R2 and Q1 may independently correspond to X1a, X2a, X3a, X4a, Y1a, Y2a, Y4a, Y5a, G1a, G2a, R1a, R2a and Q1a, or vice versa. Furthermore, Q2 represents the same as those in [1] or the general formula (A), (C) or (18),
-
- wherein, in the formula, Y1, Y2, Y3, Y4 and Y5 are the same as those described above,
-
- wherein, in the formula, Y11 and Y14 may be the same or different and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y13 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C2-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y12 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group, or
-
- wherein, in the formula, Y1a, Y2a, Y4a, Y5a, Ra, Rb and Rc represent the same as those described above.
-
- wherein, in the formula, A1, A2, A3, A4, G1, G2, R1, R2, X, n, Q1 and Q2 represent the same as those described above; and L represents a functional group having a leaving ability such as a halogen atom, a hydroxy group or the like.
- By reacting an m-nitroaromatic carboxylic acid derivative having a leaving group represented by the general formula (19) with an aromatic amine derivative represented by the general formula (20) in an appropriate solvent or without a solvent, an aromatic carboxylic acid amide derivative having a nitro group represented by the general formula (21) can be prepared. In the process, a suitable base can also be used.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile and the like; and inert solvents such as 1, 3-dimethyl-2-imidazolidinone and the like. These solvents can be used singly or in combination of 2 or more kinds.
- Furthermore, examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as di-potassium mono-hydrogen phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; and alkali metal alcoholates such as sodium methoxide, sodium ethoxide and the like. These bases may be suitably selected in the range of 0.01 to 5 mole equivalents, based on the compound represented by the general formula (19) and used accordingly.
- The reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- Of the compounds represented by the general formula (19), an aromatic carboxylic acid halide derivative can be easily prepared from an aromatic carboxylic acid according to a usual method employing a halogenating agent. Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride and the like.
- On the other hand, the compound represented by the general formula (21) can be prepared from the m-nitroaromatic carboxylic acid derivative and the compound represented by the general formula (20) without using a halogenating agent. As a method thereof, a method suitably using an additive such as 1-hydroxybenzotriazole or the like and employing a condensation agent using N,N'-dicyclohexylcarbodiimide according to a method as described, for example, in Chem. Ber. p. 788 (1970) can be exemplified. Other condensation agents to be used in this case include, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1,1'-carbonylbis-1H-imidazole and the like.
- Furthermore, as other method for preparing the compound represented by the general formula (21), a mixed anhydride procedure using chloroformate esters can be cited. Also, the compound represented by the general formula (21) can be prepared according to a method as described in J. Am. Chem. Soc. p. 5012 (1967). Examples of chloroformate esters to be used in this case include isobutyl chloroformate, isopropyl chloroformate and the like. In addition to chloroformate esters, diethylacetyl chloride, trimethylacetyl chloride and the like can be cited.
- Both the method using a condensation agent and mixed anhydride procedure are not restricted to the solvent, reaction temperature and reaction time as described in the above literatures, and an inert solvent which does not remarkably hinder the suitable progress of the reaction may be used. The reaction temperature and reaction time may be suitably selected as the reaction proceeds.
- 1-(ii): General formula (21) → General formula (22)
An aromatic carboxylic acid amide derivative having a nitro group represented by the general formula (21) can be made into an aromatic carboxylic acid amide derivative having an amino group represented by the general formula (22) by the reduction reaction. As the reduction reaction, a method employing the hydrogenation reaction and a method employing a metallic compound (for example, stannous chloride (anhydride), iron powder, zinc powder and the like) can be cited. - The former method can be carried out in a proper solvent in the presence of a catalyst, at ordinary pressure or under pressure, in a hydrogen atmosphere. Examples of the catalyst include, for example, palladium catalysts such as palladium carbon and the like, nickel catalysts such as Raney nickel and the like, cobalt catalysts, ruthenium catalysts, rhodium catalysts, platinum catalysts and the like. Examples of the solvent include, for example, water; alcohols such as methanol, ethanol and the like; aromatic hydrocarbons such as benzene, toluene and the like; chained ethers or cyclic ethers such as ether, dioxane, tetrahydrofuran and the like; and esters such as ethyl acetate and the like. The pressure may be suitably selected in the range of 0.1 to 10 MPa, the reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, and the reaction time may be properly selected in the range of several minutes to 96 hours. The compound of the general formula (22) can be more effectively prepared.
- As the latter method, a method employing stannous chloride (anhydride) as a metallic compound according to the conditions as described in "Organic Syntheses" Coll. Vol. III P. 453 can be cited.
- 1-(iii): General formula (22) + General formula (23) → General formula (24)
By reacting an aromatic carboxylic acid amide derivative having an amino group represented by the general formula (22) with a compound represented by the general formula (23) in an appropriate solvent, a compound represented by the general formula (24) of the present invention can be prepared. In this process, a suitable base can also be used. - Solvents may not remarkably hinder the progress of the reaction and examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile and the like; and inert solvents such as 1,3-dimethyl-2-imidazolidinone and the like. These solvents can be used singly or in combination of 2 or more kinds.
- Furthermore, examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as di-potassium mono-hydrogen phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; and alkali metal alcoholates such as sodium methoxide, sodium ethoxide and the like. These bases may be suitably selected in the range of 0.01 to 5 mole equivalents based on the compound represented by the general formula (22) and used accordingly. The reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours. Furthermore', a method employing a condensation agent and a mixed anhydride procedure as described in 1-(i) can also be used for the production thereof.
- 1-(iv): General formula (24) + General formula (25) → General formula (26)
By reacting a compound represented by the general formula (24) with an alkyl compound having a leaving group represented by the general formula (25) in a solvent or without a solvent, a compound represented by the general formula (26) of the present invention can be prepared. Examples of the compound represented by the general formula (25) include alkyl halides such as methyl iodide, ethyl iodide, n-propyl bromide and the like. Furthermore, in this process, a suitable base or solvent can be used. As the base or solvent, the bases or solvents cited in 1-(i) can be used. The reaction temperature and reaction time cited in 1-(i) can also be used. - Furthermore, the compound represented by the general formula (26) can also be prepared by a separate method comprising reacting an alkylating agent such as dimethyl sulfate, diethyl sulfate or the like, instead of the compound represented by the general formula (25) , with the compound represented by the general formula (24).
- Preparation Method 2
-
- wherein, in the formula, A1, A2, A3, A4, G1, G2, R1, R2, X, n, Q1, Q2, L and Hal are the same as those described above.
- 2-(i): General formula (27) + General formula (23) → General formula (28)
By reacting a carboxylic acid having an amino group represented by the general formula (27) as a starting material with a compound represented by the general formula (23) in accordance with the conditions described in 1-(i), carboxylic acids having an acylamino group represented by the general formula (28) can be prepared. - 2- (ii) : General formula (28) → General formula (29)
A compound represented by the general formula (29) can be prepared by a known usual method comprising reacting a compound represented by the general formula (28) with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride or the like. - 2-(iii) : General formula (29) + General formula (20) → General formula (30)
By reacting a compound represented by the general formula (29) with a compound represented by the general formula (20) according to the conditions described in 1-(i), a compound represented by the general formula (30) can be prepared. - 2-(iv) : General formula (28) + General formula (20) → General formula (30)
By reacting a compound represented by the general formula (28) with a compound represented by the general formula (20) according to the conditions using a condensation agent or a mixed anhydride procedure described in 1- (i), a compound represented by the general formula (30) can be prepared. - Preparation Method 3
-
- wherein, in the formula, A1, A2, A3, A4, G1, R1, R2, X, n, Q1, Q2 and L are the same as those described above.
- 3-(i): General formula (31) → General formula (32)
By reacting a compound represented by the general formula (31) with a Lawson reagent according to the known conditions described in Synthesis p. 463 (1993), Synthesis p. 829 (1984) and the like, a compound represented by the general formula (32) can be prepared. The conditions such as a solvent, reaction temperature and the like are not restricted to those described in the literatures. - 3-(ii): General formula (32) + General formula (23) → General formula (33)
By reacting a compound represented by the general formula (32) with a compound represented by the general formula (23) according to the conditions described in 1-(i), a compound represented by the general formula (33) can be prepared. - Preparation Method 4
-
- wherein, in the formula, A1, A2, A3, A4, R1, R2, X, n, Q1 and Q2 are the same as those described above.
Compounds represented by the general formulae (35) and (36) can be prepared from a compound represented by the general formula (34) according to the conditions described in 3-(i). The conditions such as a solvent, reaction temperature and the like are not restricted to those described in the literatures. These two compounds can be easily separated and purified by a known separation and purification technique such as silica gel column chromatography and the like. - Preparation Method 5
-
- wherein, in the formula, A1, A2, A3, A4, G1, G2, R1, R2, X, n, Q1, Q2, L and Hal are the same as those described above.
- 5-(i): General formula (37) → General formula (38)
A compound represented by the general formula (38) can be prepared by carrying out an amination reaction using ammonia according to the conditions described, for example, in J. Org. Chem. p. 280 (1958). However, the conditions such as a reaction solvent and the like are not restricted to those described in the literatures, and an inert solvent which does not remarkably hinder the proper progress of the reaction may be used. The reaction temperature and reaction time may be suitably selected as the reaction proceeds. Furthermore, examples of the amination agent include methylamine, ethylamine or the like, in addition to ammonia . - 5-(ii): General formula (38) + General formula (23) → General formula (39)
By reacting a compound represented by the general formula (38) with a compound represented by the general formula (23) according to the conditions described in 1-(i), a compound represented by the general formula (39) can be prepared. - Preparation Method 6
-
- wherein, in the formula, R2 represents the same as those described above; Y1 and Y5 independently represent a methyl group, a chlorine atom, a bromine atom or an iodine atom; Y2 and Y4 represent the same as those described above; Rf represents a C1-C6 perfluoroalkyl group; and m represents 1 or 2.
- 6-(i): General formula (40) + General formula (41) → General formula (42)
By reacting aminothiophenols represented by the general formula (40) with haloalkyl iodide represented by the general formula (41) in accordance with a method described in J. Fluorine Chem. p. 207 (1994), a compound represented by the general formula (42) can be prepared. - Examples of haloalkyl iodide represented by the general formula (41) include trifluoromethyl iodide, pentafluoroethyl iodide, heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide, nonafluoro-n-butyl iodide, nonafluoroisobutyl iodide and the like. These may be suitably used in the range of 1 to 10 mole equivalents, based on the compound represented by the general formula (40).
- The solvent to be used in the process is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction. Examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile and the like; and inert solvents such as 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide and the like. These solvents can be used singly or in combination of 2 or more kinds. Particularly preferable is a polar solvent. The reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- 6-(ii): General formula (42) → General formula (43)
A compound represented by the general formula (43) can be prepared by using a suitable halogenating agent. For example, a method as described in Synth. Commun. p. 1261 (1989) can be cited. - Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinic acid imide, N-bromosuccinic acid imide, N-iodosuccinic acid imide and the like. These may be suitably used in the range of 1 to 10 mole equivalents, based on a compound represented by the general formula (42).
- In the process, an appropriate solvent can also be used, but a solvent in use is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction. Examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichlbromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile and the like; and inert solvents such as 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide and the like. These solvents can be used singly or in combination of 2 or more kinds. Particularly preferable is a polar solvent. The reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- 6-(iii): General formula (43) → General formula (44)
A compound represented by the general formula (44) can be prepared by using a suitable oxidant. A method described, for example, in Tetrahedron Lett. p. 4955 (1994) can be cited. Examples of the oxidant include organic peroxides such as m-chloroperbenzoic acid and the like, sodium metaperiodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, dinitrogen tetraoxide, acyl nitrate, iodine, bromine, N-bromosuccinic acid imide, iodosylbenzyl, t-butyl hypochlorite and the like. The solvent to be used in this process is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction. These solvents can be used singly or in combination of 2 or more kinds. Particularly preferable is a polar solvent. The reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours. - 6-(iv): General formula (43) → General formula (43-2)
A compound represented by the general formula (43-2) (wherein, in the formula, any one of Y1 and Y5 must represent a methyl group) can be prepared from a compound represented by the general formula (43) by using a suitable methylating agent. In this process, a method described, for example, in Tetrahedron Lett. p. 6237 (2000) can be cited. - 6-(v): General formula (43-2) → General formula (44-2)
A compound represented by the general formula (44-2) (wherein, in the formula, any one of Y1 and Y5 must represent a methyl group) can be prepared according to the method described in 6-(iii). - Furthermore, the compound of the present invention can be prepared by suitably selecting a preparation method as illustrated in the present invention using an aniline derivative represented by the general formula (43), (44), (43-2) or (44-2).
- Preparation Method 7
-
- wherein, in the formula, R2, Y1, Y2, Y4, Y5, Rf and m represent the same as those described in the preparation method 6.
An aniline derivative represented by the general formula (47) can be prepared using a compound represented by the general formula (45) as a starting raw material according to the preparation method 6. Furthermore, by suitably selecting a preparation method as illustrated in the present invention, the compound of the present invention can be prepared. - Preparation Method 8
-
- wherein, in the formula, A1, A2, A3, A4, X, n, G2, R2 and Q2 represent the same as those above.
By reacting a compound represented by the general formula (48) with a suitable reactant using an appropriate base in a proper solvent, a compound represented by the general formula (49) can be prepared. - Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide; water and the like. These solvents can be used singly or in combination of 2 or more kinds.
- Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as potassium mono-hydrogen phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and the like; organolithiums such as n-butyl lithium and the like; and Grignard reagents such as ethyl magnesium bromide and the like.
- These bases may be suitably selected in the range of 0.01 to 5 mole equivalents, based on the compound represented by the general formula (48) or may be used as a solvent.
- Examples of the reactant include halogenated alkyls such as methyl iodide, ethyl bromide, trifluoromethyl iodide, 2,2,2-trifluoroethyl iodide and the like; halogenated allyls such as allyl iodide and the like; halogenated propargyls such as propargyl bromide and the like; halogenated acyls such as acetyl chloride and the like; acid anhydrides such as trifluoroacetic anhydride and the like; and alkyl sulfuric acids such as dimethyl sulfate, diethyl sulfate and the like.
- These reactants may be suitably selected in the range of 1 to 5 mole equivalents, based on the compound represented by the general formula (48) or may be used as a solvent.
- The reaction temperature may be suitably selected in the range of -80 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- Preparation Method 9
-
- wherein, in the formula, A1, A2, A3, A4, X, n, G2, R1, R2 and Q2 represent the same as those described above.
- 9-(i): General formula (22) → General formula (50)
By reacting a compound represented by the general formula (22) with aldehydes or ketones in an appropriate solvent, adding a suitable catalyst and reacting the resultant in a hydrogen atmosphere, a compound represented by the general formula (50) can be prepared. - Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.
- Examples of the catalyst include palladium catalysts such as palladium carbon, palladium hydroxide carbon and the like, nickel catalysts such as Raney nickel and the like, cobalt catalysts, platinum catalysts, ruthenium catalysts, rhodium catalysts and the like.
- Examples of aldehydes include formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde and the like.
- Examples of ketones include acetone, perfluoroacetone, methylethyl ketone and the like.
- The reaction pressure may be suitably selected in the range of 1 to 100 atm.
- The reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- 9-(ii): General formula (22) → General formula (50) (separate method 1)
By reacting a compound represented by the general formula (22) with aldehydes or ketones in an appropriate solvent, and applying a suitable reducing agent, a compound represented by the general formula (50) can be prepared. - Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.
- Examples of the reducing agent include borohydrides such as sodium borohydride, sodium cyanoborohydride, sodium triacetate borohydride and the like.
- Examples of aldehydes include formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde and the like.
- Examples of ketones include acetone, perfluoroacetone, methylethyl ketone and the like.
- The reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- 9-(iii) : General formula (22) → General formula (50) (separate method 2)
By reacting a compound represented by the general formula (22) with a formylating agent in an appropriate solvent or without a solvent and applying a proper additive, it is possible to prepare a compound, wherein, in the general formula (50), R1 is a methyl group. - Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.
- Examples of the formylating agent include formic anhydrides such as formaldehyde, formic acid, fluoroformic acid, formyl (2, 2-dimethylpropionic acid) and the like; formic acid esters such as phenyl formate and the like; pentafluorobenzaldehyde, oxazole and the like.
- Examples of the reducing agent include inorganic acids such as sulfuric acid and the like; organic acids such as formic acid and the like; borohydrides such as sodium borohydride, sodium cyanoborohydride and the like; boronic acid, lithium aluminum hydride and the like.
- The reaction temperature may be suitably selected in the range of -20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- Preparation Method 10
-
- wherein, in the formula, X1a, X2a, X3a, X4a, Y1a, Y2a, Y4a, Y5a, G2a, R2a, Ra and Rb represent the same as those described above; in the general formula (51), Rc' represents a hydroxy group or -O-Rd (Rd represents the same as those described above); and in the general formula (52), Rc" represents a chlorine atom, a bromine atom or an iodine atom.
- By reacting a compound represented by the general formula (51) with a suitable halogenating agent in an appropriate solvent or without a solvent, a chlorine compound (a bromine compound or an iodine compound) represented by the general formula (52) can be prepared. In the process, an appropriate additive can also be used.
- Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.
- Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, Rydon reagents, sulfonyl halides such as methanesulfonyl chloride, p-toluenesulfonyl chloride, benzenesulfonyl chloride and the like, sulfonium halides, sulfonate esters, chlorine, bromine, iodine, hypohalite esters, N-halogenoamines, hydrogen chloride, hydrogen bromide, sodium bromide, potassium bromide, cyanuric chloride, 1,3-dichloro-1,2,4-triazole, titanium (IV) chloride, vanadium (IV) chloride, arsenic (III) chloride, N,N-diethyl-1,2,2-trichlorovinylamine, trichloroacetonitrile, sodium chloride, ammonium bromide, N,N-dimethylchloroforminium chloride, N,N-dimethylchloroforminium bromide, phosphorus trichloride, phosphorus tribromide, N,N-dimethyl phosphoamidine dichloride and the like.
- Examples of the additive include metal salts such as zinc chloride, lithium bromide and the like; organic bases such as a phase transfer catalyst, hexamethylphosphoric triamide and the like; inorganic acids such as sulfuric acid and the like; N,N-dimethylformamide and the like.
- These halogenating agents may be suitably selected in the range of 0.01 to 10 mole equivalents, based on the compound represented by the general formula (1) or may be used as a solvent.
- The reaction temperature may be suitably selected in the range of -80 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- Preparation Method 11
-
- wherein, in the formula, X1a, X2a, X3a, X4a, Y1a, Y2a, Y4a, Y5a, G2a, R1a, R2a, Ra, Rb and Rc represent the same as those described above.
By reacting a compound represented by the general formula (53) with a suitable fluorinating agent in an appropriate solvent or without a solvent, a compound represented by the general formula (54) can be prepared. - Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.
- Examples of the fluorinating agent include 1,1,2,2-tetrafluoroethyldiethylamine, 2-chloro-1,1,2-trifluoroethyldiethylamine, trifluorodiphenylphosphorane, difluorotriphenylphosphorane, fluoroformate esters, sulfur tetrafluoride, potassium fluoride, potassium hydrogen fluoride, cesium fluoride, rubidium fluoride, sodium fluoride, lithium fluoride, antimony (III) fluoride, antimony (V) fluoride, zinc fluoride, cobalt fluoride, lead fluoride, copper fluoride, mercury (II) fluoride, silver fluoride, silver fluoroborate, thallium (I) fluoride, molybdenum (VI) fluoride, arsenic (III) fluoride, bromine fluoride, selenium (IV) fluoride, tris(dimethylamino)sulfonium difluorotrimethylsilicate, sodium hexafluorosilicate, quaternary ammonium fluoride, (2-chloroethyl)diethylamine, diethylaminosulfur trifluoride, morpholinosulfur trifluoride, silicon tetrafluoride, hydrogen fluoride, hydrofluoric acid, hydrogen fluoride pyridine complex, hydrogen fluoride triethylamine complex, hydrogen fluoride salt, bis(2-methoxyethyl)aminosulfur trifluoride, 2,2-difluoro-1,3-dimethyl-2-imidazolidinone, iodine pentafluoride, tris(diethylamino)phosphonium-2,2,3,3,4,4-hexafluoro-cyclobuta ne ylide, triethylammonium hexafluorocyclobutane ylide, hexafluoropropene and the like. These fluorinating agents can be used singly or in combination of 2 or more kinds. These halogenating agents may be suitably selected in the range of 1 to 10 mole equivalents, based on the compound represented by the general formula (53) or may be suitably used as a solvent.
- An additive may also be used and examples thereof include crown ethers such as 18-crown-6 and the like; phase transfer catalysts such as tetraphenylphosphonium salts and the like; inorganic salts such as calcium fluoride, calcium chloride and the like; metal oxides such as mercury oxide and the like; ion exchange resins and the like. These additives can be not only added in the reaction system,_ but also used as a pretreatment agent of the fluorinating agent.
- The reaction temperature may be suitably selected in the range of -80 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.
- Preparation Method 12
-
- wherein, in the formula, X1a, X2a, X3a, X4a, Y1a, Y2a, Y4a, Y5a, G2a, R1a, R2a, Ra, Rb, Rc' and Rc'' represent the same as those described above.
A compound represented by the general formula (56) can be prepared from a compound represented by the general formula (55) according to the method described in the preparation method 10. - Preparation Method 13
-
- wherein, in the formula, X1a, X2a, X3a, X4a, Y1a, Y2a, Y4a, Y5a, G1a, G2a, R1a, R2a, Ra, Rb, Rc and Q1a represent the same as those described above.
A compound represented by the general formula (58) can be prepared from a compound represented by the general formula (57) according to the method described in the preparation method 11. - Preparation Method 14
-
- wherein, in the formula, X1a, X2a, X3a, X4a, Y1a, Y2a, Y4a, Y5a, G1a, G2a, R1a, R2a, Ra, Rb, Rc', Rc" and Q1a represent the same as those described above.
A compound represented by the general formula (60) can be prepared from a compound represented by the general formula (59) according to the method described in the preparation method 10. - In all preparation methods as illustrated above, desired products may be isolated according to a usual method from the reaction system after completion of the reaction, and can be purified, if needed, by carrying out operations such as recrystallization, column chromatography, distillation and the like. Furthermore, desired products can also be supplied to the next reaction process without isolating them from the reaction system.
- The compound represented by the general formula (2) can be prepared according to a method as described in International Publication No.
2005 / 21488 - The compound represented by the general formula (3) can be prepared according to a method as described in International Publication No.
2003 / 8372 - The compound represented by the general formula (4) can be prepared according to a method as described in International Publication No.
2005 / 42474 - Typical compounds of the compound represented by the general formula (1) that is an active ingredient of an insecticide of the present invention are illustrated in Tables 1 to 5 below, but the present invention is not restricted thereto.
- Incidentally, in the tables, "n-" refers to normal, "Me" refers to a methyl group, "Et" refers to an ethyl group, "n-Pr" refers to a normal propyl group, "i-Pr" refers to an isopropyl group, "n-Bu" refers to a normal butyl group, "i-Bu" refers to an isobutyl group, "s-Bu" refers to a secondary butyl group, "t-Bu" refers to a tertiary butyl group, "H" refers to a hydrogen atom, "O" refers to an oxygen atom, "S" refers to a sulfur atom, "C" refers to a carbon atom, "N" refers to a nitrogen atom, "F" refers to a fluorine atom, "Cl" refers to a chlorine atom, "Br" refers to a bromine atom, "I" refers to an iodine atom, "CF3" refers to a trifluoromethyl group, "MeS" refers to a methylthio group, "MeSO" refers to a methylsulfinyl group, "MeSO2" refers to a methylsulfonyl group, "MeO" refers to a methoxy group, "NH2" refers to an amino group, "MeNH" refers to a methylamino group, "Me2N" refers to a dimethylamino group, and "OH" refers to a hydroxy group.
-
[Table 1-1] Compound Nos. Q1 Q2 1 phenyl 2,6-dimethyl-4-(pentafluoroethyl)phenyl 2 phenyl 2,6-dichloro-4-(pentafluoroethyl)phenyl 3 2-fluorophenyl 2,6-dichloro-4-(pentafluoroethyl)phenyl 4 phenyl 2,6-dibromo-4-(pentafluoroethyl)phenyl 5 2-fluorophenyl 2,6-dibromo-4-(pentafluoroethyl)phenyl 6 phenyl 2,6-dichloro-4-(heptafluoroisopropyl) phenyl 7 phenyl 2,6-dibromo-4-(heptafluoroisopropyl) phenyl 8 2-fluorophenyl 2,6-dibromo-4-(heptafluoroisopropyl) phenyl 9 phenyl 2,6-dimethyl-4-(heptafluoro-n-propyl) phenyl 10 phenyl 2, 6-dimethyl-4-(heptafluoroisopropyl) phenyl 11 2-methylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 12 3-methylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 13 4-methylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 14 2-ethylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 15 3-ethylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 16 4-ethylphenyl 2,-6-dimethyl-4-(heptafluoroisopropyl) phenyl 17 2-fluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 18 3-fluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 19 4-fluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 20 2-chlorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl -
[Table 1-2] Compound Nos. Q1 Q2 21 3-chlorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 22 4-chlorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 23 2-bromophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 24 3-bromophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 25 4-bromophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 26 2-iodophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 27 3-iodophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 28 4-iodophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 29 3-cyanophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 30 4-cyanophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 31 2-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 32 3-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 33 4-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 34 2-aminophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 35 3-aminophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 36 4-aminophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 37 2-trifluoro methylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 38 3-trifluoro methylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 39 4-trifluoro methylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 40 2-hydroxyphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl -
[Table 1-3] Compound Nos. Q1 Q2 41 2-methoxyphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 42 3-methoxyphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 43 4-methoxyphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 44 2-phenoxyphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 45 4-(1,1-dimethyl ethyl)phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 46 3-(dimethylamino) phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 47 4-(dimethylamino) phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 48 4-trifluoro methoxyphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 49 2-(acetylamino) phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 50 3-(acetylamino) phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 51 4-(acetylamino) phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 52 2-acetoxyphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 53 2-(methoxy carbonyl)phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 54 4-(methoxy carbonyl)phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 55 2-(4-trifluoro methylphenyl) phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 56 2,3-dimethylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 57 2,4-dimethylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 58 2,6-dimethylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 59 2,3-difluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 60 2,4-difluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl -
[Table 1-4] Compound Nos. Q1 Q2 61 2,5-difluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 62 2,6-difluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 63 3,4-difluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 64 3,5-difluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 65 2,3-dichlorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 66 2,4-dichlorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 67 2,5-dichlorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 68 2,6-dichlorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 69 3,4-dichlorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 70 2,4-dinitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 71 3,4-dinitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 72 2,6-dimethoxy phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 73 3,5-dimethoxy phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 74 3-methyl-4-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 75 5-amino-2-fluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 76 3-fluoro-2-methylphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 77 2-fluoro-5-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 78 4-fluoro-3-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 79 5-fluoro-2-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 80 2-fluoro-6-iodophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl -
[Table 1-5] Compound Nos. Q1 Q2 81 2-fluoro-5-trifluoromethyl phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 82 2-chloro-4-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 83 2-chloro-4-fluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 84 2-chloro-6-fluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 85 3-chloro-4-fluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 86 4-chloro-2-fluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 87 4-chloro-2-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 88 3-methoxy-4-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 89 2-methoxy-4-nitrophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 90 2,3,4-trifluoro phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 91 2,4,6-trimethyl phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 92 2,3,6-trifluoro phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 93 2,4,5-trimethoxy phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 94 3,4,5-trimethoxy phenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 95 2,3,4,5,6-pentafluorophenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 96 2-biphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 97 3-biphenyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 98 1-naphthyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 99 2-naphthyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 100 pyridine-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl -
[Table 1-6] Compound Nos. Q1 Q2 101 pyridine-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 102 pyridine-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 103 2-methyl pyridine-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 104 3-methyl pyridine-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 105 2-fluoro pyridine-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 106 2-chloro pyridine-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 107 2-chloro pyridine-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 108 2-chloro pyridine-6-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 109 2-chloro pyridine-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 110 5-chloro pyridine-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 111 4-trifluoromethyl pyridine-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 112 3-hydroxy pyridine-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 113 2-phenoxy pyridine-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 114 2-methylthio pyridine-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 115 2,6-dimethoxy pyridine-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 116 2,3-dichloro pyridine-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 117 2,5-dichloro pyridine-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 118 2,6-dichloro pyridine-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 119 3,5-dichloro pyridine-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 120 pyridine-N-oxide-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl -
[Table 1-7] Compound Nos. Q1 Q2 121 N-methylpyrrole-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 122 pyrazine-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 123 2-methyl pyrazine-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 124 4-trifluoromethyl pyrimidine-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 125 furan-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 126 furan-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 127 2-tetrahydro furanyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 128 3-tetrahydro furanyl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 129 benzofuran-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 130 tetrahydropyran-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 131 2-methyl-5,6-dihydro-4H pyran-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 132 thiophene-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 133 thiophene-3-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 134 3-methyl thiophene-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 135 2-nitrothiophene-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 136 2-methylthiophene-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 137 3-chlorothiophene-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 138 2-chlorothiophene-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 139 3-bromothiophene-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 140 2-bromothiophene-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl -
[Table 1-8] Compound Nos. Q1 Q2 141 3-iodothiophene-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 142 3-phenylthiophene-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 143 2,4-dimethyl thiophene-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 144 benzothiophene-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 145 4-nitro-1H-pyrrole -2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 146 3-ethyl-3H-pyrazole-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 147 1-methyl-3-nitro-1H-pyrazole-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 148 3-chloro-1-methyl-1H-pyrazole-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 149 3-bromo-1-methyl-1H-pyrazole-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl), phenyl 150 1-methyl-3-trifluoromethyl-1H-pyrazole-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 151 1-methyl-5-trifluoromethyl-1H-pyrazole-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 152 isoxazole-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 153 4-trifluoro methylthiazole-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 154 2,4-dimethyl thiazole-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 155 2-ethyl-4-methyl thiazole-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 156 2-chloro-4-methyl thiazole-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 157 3-methyl isothiazole-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 158 3,4-dichloro-isothiazole-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 159 3-chlorobenzo thiazole-2-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 160 2,2-difluoro-benzo [1.3]dioxole-5-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl -
[Table 1-9] Compound Nos. Q1 Q2 161 2,2-difluoro-benzo [1.3]dioxole-4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 162 2-phenylquinoline -4-yl 2,6-dimethyl-4-(heptafluoroisopropyl) phenyl 163 phenyl 2-bromo-4-(heptafluoroisopropyl)-6-methylphenyl 164 phenyl 2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl 165 2-fluorophenyl 2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl 166 phenyl 4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl 167 phenyl 4-(heptafluoroisopropyl)-2-hydroxy-6-methylphenyl 168 phenyl 2-chloro-6-ethyl-4-(heptafluoro isopropyl)phenyl 169 phenyl 2-bromo-6-ethyl-4-(heptafluoro isopropyl)phenyl 170 2-fluorophenyl 2-bromo-6-ethyl-4-(heptafluoro isopropyl)phenyl 171 phenyl 2-ethyl-4-(heptafluoroisopropyl)-6-iodophenyl 172 2-fluorophenyl 2-ethyl-4-(heptafluoroisopropyl)-6-iodophenyl 173 4-nitrophenyl 2-ethyl-4-(heptafluoroisopropyl)-6-iodophenyl 174 4-cyanophenyl 2-ethyl-4-(heptafluoroisopropyl)-6-iodophenyl 175 4-nitrophenyl 4-(heptafluoroisopropyl)-2-methyl-6-n-propylphenyl 176 phenyl 4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl 177 2-fluorophenyl 4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl 178 phenyl 2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl 179 2-fluorophenyl 2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl 180 4-nitrophenyl 2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl -
[Table 1-10] Compound Nos. Q1 Q2 181 4-cyanophenyl 2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl 182 phenyl 4-(heptafluoroisopropyl)-2-iodo-6-n-propylphenyl 183 2-fluorophenyl 4-(heptafluoroisopropyl)-2-iodo-6-n-propylphenyl 184 4-nitrophenyl 4-(heptafluoroisopropyl)-2-iodo-6-n-propylphenyl 185 4-cyanophenyl 4-(heptafluoroisopropyl)-2-iodo-6-n-propylphenyl 186 4-trifluoromethyl phenyl 4-(heptafluoroisopropyl)-2-iodo-6-n-propylphenyl 187 phenyl 2-chloro-4-(heptafluoroisopropyl)-6-n-butylphenyl 188 2-fluorophenyl 2-chloro-4-(heptafluoroisopropyl)-6-n-butylphenyl 189 phenyl 2-bromo-4-(heptafluoroisopropyl)-6-n-butylphenyl 190 2-fluorophenyl 2-bromo-4-(heptafluoroisopropyl)-6-n-butylphenyl 191 phenyl 4-(heptafluoroisopropyl)-2-iodo-6-n-butylphenyl 192 2-fluorophenyl 4-(heptafluoroisopropyl)-2-iodo-6-n-butylphenyl 193 phenyl 2-(2-butyl)-6-chloro-4-(heptafluoro isopropyl)phenyl 194 phenyl 2-bromo-6-(2-butyl)-4-(hepta fluoroisopropyl)phenyl 195 2-fluorophenyl 2-bromo-6-(2-butyl)-4-(hepta fluoroisopropyl)phenyl 196 phenyl 2-(2-butyl)-4-(heptafluoroisopropyl)-6-iodophenyl 197 2-fluorophenyl 2-bromo-6-cyano-4-(heptafluoro isopropyl)phenyl 198 phenyl 2-bromo-4-(heptafluoroisopropyl)-6-methylthiophenyl 199 2-fluorophenyl 2-bromo-4-(heptafluoroisopropyl)-6-methylthiophenyl 200 phenyl 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfinyl)phenyl -
[Table 1-11] Compound Nos. Q1 Q2 201 2-fluorophenyl 2-chloro-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 202 2-chloropyridine-3-yl 2-chloro-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 203 phenyl 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 204 2-fluorophenyl 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 205 4-fluorophenyl 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 206 4-nitrophenyl 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 207 4-cyanophenyl 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 208 2-chloropyridine-3-yl 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 209 phenyl 4-(heptafluoroisopropyl)-2-methyl thiomethyl-6-trifluoromethylphenyl 210 phenyl 2-bromo-4-(heptafluoroisopropyl)-6-(trifluoromethylthio)phenyl 211 phenyl 2,6-dimethyl-4-(nonafluoro-n-butyl) phenyl 212 phenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 213 2-methylphenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 214 4-methylphenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 215 2-fluorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 216 3-fluorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 217 4-fluorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 218 2-chlorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 219 4-chlorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 220 2-bromophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl -
[Table 1-12] Compound Nos. Q1 Q2 221 2-iodophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 222 3-cyanophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 223 4-cyanophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 224 2-nitrophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 225 3-nitrophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 226 4-nitrophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 227 2-trifluoromethyl phenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 228 4-trifluoromethyl phenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 229 4-trifluoromethoxy phenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 230 2,3-difluorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 231 2,4-difluorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 232 2,5-difluorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 233 2,6-difluorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 234 2,4-dichlorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl)-phenyl 235 2,6-dichlorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 236 3,4-dichlorophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 237 2-chloro-4-nitro phenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 238 2-chloro-4-fluoro phenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 239 2-chloro-6-fluoro phenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 240 4-chloro-2-fluoro phenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl -
[Table 1-13] Compound Nos. Q1 Q2 241 4-chloro-2-nitrophenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 242 2,3,6-trifluoro phenyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 243 pyridine-2-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 244 pyridine-3-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 245 2-fluoropyridine-3-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 246 2-chloropyridine-3-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 247 2-chloropyridine-5-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 248 2-methylthio pyridine-3-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 249 pyrazine-2-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 250 furan-2-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 251 furan-3-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 252 2-tetrahydro furanyl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 253 benzofuran-2-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 254 thiophene-2-yl 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 255 2,6-difluorophenyl 2,6-dichloro-4-(trifluoromethylthio) phenyl 256 phenyl 2,6-dibromo-4-(trifluoromethylthio) phenyl 257 2,6-difluorophenyl 2,6-dibromo-4-(trifluoromethylthio) phenyl 258 phenyl 2,6-dibromo-4-(pentafluoroethylthio) phenyl 259 2-fluorophenyl 2,6-dibromo-4-(pentafluoroethylthio) phenyl 260 phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl -
[Table 1-14] Compound Nos. Q1 Q2 261 2-fluorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 262 phenyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 263 phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 264 2-methylphenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 265 4-methylphenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 266 2-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 267 3-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 268 4-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 269 2-chlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 270 4-chlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 271 2-bromophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 272 2-iodophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 273 3-cyanophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 274 4-cyanophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 275 2-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 276 3-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 277 4-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 278 2-trifluoromethyl phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 279 4-trifluoromethyl phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 280 4-trifluoromethoxy phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 1-15] Compound Nos. Q1 Q2 281 2,3-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 282 2,4-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 283 2,5-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 284 2,6-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 285 3-aminophenyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl 286 3-(acetylamino) phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 287 3-(methylsulfonyl amino)phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 288 2,4-dinitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 289 3,4-dinitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 290 3-methyl-4-nitro phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 291 5-amino-2-fluoro phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl. 292 2-fluoro-5-nitro phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 293 2-fluoro-5-(methyl sulfonylamino) phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 294 2-methoxy-4-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 295 3-methoxy-4-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 296 5-(acetylamino)-2-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 297 2,4-dichlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 298 2,6-dichlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 299 3,4-dichlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 300 2-chloro-4-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 1-16] Compound Nos. Q1 Q2 301 2-chloro-4-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 302 2-chloro-6-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 303 4-chloro-2-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 304 4-chloro-2-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 305 2,3,6-trifluoro phenyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 306 pyridine-2-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 307 pyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 308 2-fluoropyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 309 2-chloropyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 310 2-chloropyridine-5-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 311 2-methylthio pyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 312 2,6-dichloro pyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 313 2,6-dichloro pyridine-4-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 314 2-chloro-6-methyl pyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 315 pyridine-N-oxide-2-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 316 pyrazine-2-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 317 1-methyl-3-nitro-1H-pyrazole-4-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 318 1-methyl-3-tri fluoromethyl-1H-pyrazole-4-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 319 1-methyl-5-tri fluoromethyl-1H-pyrazole-4-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 320 2-tetrahydro furanyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 1-17] Compound Nos. Q1 Q2 321 2-phenylthiazole-4-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 322 furan-2-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 323 furan-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 324 2-tetrahydro furanyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 325 benzofuran-2-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 326 thiophene-2-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 327 phenyl 2,6-diiodo-4-(heptafluoro-n-propylthio)phenyl 328 2-fluorophenyl 2,6-diiodo-4-(heptafluoro-n-propylthio)phenyl 329 phenyl 2,6-dichloro-4-(heptafluoro isopropylthio)phenyl 330 2-fluorophenyl 2,6-dichloro-4-(heptafluoro isopropylthio)phenyl 331 2-chloropyridine-3-yl 2,6-dichloro-4-(heptafluoro isopropylthio)phenyl 332 phenyl 2,6-dibromo-4-(heptafluoro isopropylthio)phenyl 333 phenyl 2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl 334 2-fluorophenyl 2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl 335 phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 336 2-methylphenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 337 4-methylphenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 338 2-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 339 3-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 340 4-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 1-18] Compound Nos. Q1 Q2 341 2-chlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 342 4-chlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 343 2-bromophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 344 2-iodophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 345 3-cyanophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 346 4-cyanophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 347 2-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 348 3-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 349 4-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 350 2-trifluoromethyl phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 351 4-trifluoromethyl phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 352 4-trifluoromethoxy phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 353 2,3-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 354 2,4-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 355 2,5-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 356 2,6-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 357 2,4-dichlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 358 2,6-dichlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 359 3,4-dichlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 360 2-chloro-4-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 1-19] Compound Nos. Q1 Q2 361 2-chloro-4-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 362 2-chloro-6-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 363 4-chloro-2-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 364 4-chloro-2-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 365 2,3,6-trifluoro phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 366 pyridine-2-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 367 pyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 368 2-fluoropyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 369 2-chloropyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 370 2-chloropyridine-5-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 371 2-methylthio pyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 372 pyrazine-2-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 373 furan-2-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 374 thiophene-2-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 375 2,6-difluorophenyl 2,6-dichloro-4-(trifluoromethyl sulfonyl)phenyl 376 phenyl 2,6-dibromo-4-(trifluoromethyl sulfonyl)phenyl 377 2,6-difluorophenyl 2,6-dibromo-4-(trifluoromethyl sulfonyl)phenyl 378 2-fluorophenyl 2,6-dichloro-4-(heptafluoro isopropylsulfonyl)phenyl 379 phenyl 2,6-dichloro-4-(heptafluoro isopropylsulfonyl)phenyl 380 phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl -
[Table 1-20] Compound Nos. Q1 Q2 381 2-methylphenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 382 4-methylphenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 383 2-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 384 3-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 385 4-fluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 386 2-chlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 387 4-chlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 388 2-bromophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 389 2-iodophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 390 3-cyanophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 391 4-cyanophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 392 2-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 393 3-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 394 4-nitrophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 395 2-trifluoromethyl phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 396 4-trifluoromethyl phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 397 4-trifluoromethoxy phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 398 2,3-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 399 2,4-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 400 2,5-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl -
[Table 1-21] Compound Nos. Q1 Q2 401 2,6-difluorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 402 2,4-dichlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 403 2,6-dichlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 404 3,4-dichlorophenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 405 2-chloro-4-nitro phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 406 2-chloro-4-fluoro phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 407 2-chloro-6-fluoro phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 408 4-chloro-2-fluoro phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 409 4-chloro-2-nitro phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 410 2,3,6-trifluoro phenyl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 411 pyridine-2-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 412 pyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 413 2-fluoropyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 414 2-chloropyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 415 2-chloropyridine-5-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 416 2-methylthio pyridine-3-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 417 pyrazine-2-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 418 furan-2-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 419 thiophene-2-yl 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 420 phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl -
[Table 1-22] Compound Nos. Q1 Q2 421 2-methylphenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 422 4-methylphenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 423 2-fluorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 424 3-fluorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 425 4-fluorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 426 2-chlorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 427 4-chlorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 428 2-bromophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 429 2-iodophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 430 3-cyanophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 431 4-cyanophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 432 2-nitrophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 433 3-nitrophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 434 4-nitrophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 435 2-trifluoromethyl phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 436 4-trifluoromethyl phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 437 4-trifluoromethoxy phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 438 2,3-difluorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 439 2,4-difluorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 440 2,5-difluorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl -
[Table 1-23] Compound Nos. Q1 Q2 441 2,6-difluorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 442 2,4-dichlorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 443 2,6-dichlorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 444 3,4-dichlorophenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 445 2-chloro-4-nitro phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 446 2-chloro-4-fluoro phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 447 2-chloro-6-fluoro phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 448 4-chloro-2-fluoro phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 449 4-chloro-2-nitro phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 450 2,3,6-trifluoro phenyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 451 pyridine-2-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 452 pyridine-3-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 453 2-fluoropyridine-3-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 454 2-chloropyridine-3-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 455 2-chloropyridine-5-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 456 2-methylthio pyridine-3-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 457 pyrazine-2-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 458 furan-2-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 459 thiophene-2-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 460 2,6-difuorophenyl 2,6-dichloro-4-(trifluoromethyl sulfonyl)phenyl -
[Table 1-24] Compound Nos. Q1 Q2 461 phenyl 2-bromo-6-(heptafluoroisopropyloxy)-4-methylpyridine-3-yl 462 2-fluorophenyl 2-bromo-6-(heptafluoroisopropyloxy)-4-methylpyridine-3-yl 463 phenyl 2,4-dimethyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl 464 phenyl 2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl 465 phenyl 2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl 466 2-fluorophenyl 2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl 467 phenyl 2-iodo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl -
[Table 2-1] Compound Nos. Q1 X1 X2 X3 X4 Q2 601 phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 602 2-methylphenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 603 3-methylphenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 604 4-methylphenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 605 2-nitrophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 606 3-nitrophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 607 4-nitrophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 608 3-cyanophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 609 4-cyanophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 610 2-fluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 611 3-fluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 612 4-fluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 613 2-chlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 614 4-chlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 615 2-bromophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 616 2-iodophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 617 2-trifluoromethyl phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 618 4-trifluoromethyl phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 619 4-trifluoromethoxy phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 620 4-(dimethylamino) phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 2-2] Compound Nos. Q1 X1 X2 X3 X4 Q2 621 2,3-difluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 622 2,4-difluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 623 2,5-difluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 624 2,6-difluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 625 2,4-dichlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 626 2,6-dichlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 627 3,4-dichlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 628 2-fluoro-4-nitro phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 629 4-fluoro-2-nitro phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 630 2-chloro-4-fluoro phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 631 4-chloro-2-fluoro phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 632 2-chloro-6-fluoro phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 633 2-chloro-4-nitro phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 634 4-chloro-2-nitro phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 635 2,3,6-trifluoro phenyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 636 pyridine-2-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 637 pyridine-3-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 638 2-fluoropyridine-3-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 639 2-chloropyridine-3-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 640 2-chloropyridine-5-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 2-3] Compound Nos. Q1 X1 X2 X3 X4 Q2 641 2-methylthio pyridine-3-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 642 pyrazine-2-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 643 furan-2-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 644 furan-3-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 645 2-tetrahydrofuranyl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 646 benzofuran-2-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 647 thiophene-2-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 648 2-methyl-5,6-dihydro-4H-pyran-3-yl F H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 649 phenyl H C1 H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 650 phenyl H F H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 651 4-nitrophenyl H F H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 652 4-cyanophenyl H F H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 653 2-fluorophenyl H F H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 654 4-fluorophenyl H F H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 655 4-trifluoromethyl phenyl H F H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 656 2,4-difluorophenyl H F H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 657 2-chloropyridine-3-yl H F H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 658 phenyl H H CF3 H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 659 phenyl H H H F 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 660 phenyl H H H C1 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 2-4] Compound Nos. Q1 X1 X2 X3 X4 Q2 661 phenyl H H H Br 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 662 phenyl H H H I 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 663 phenyl F H H F 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 664 phenyl H Br H Br 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 665 phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 666 2-methylphenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 667 4-methylphenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 668 2-fluorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 669 3-fluorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 670 4-fluorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 671 2-chlorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 672 4-chlorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 673 2-bromophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 674 2-iodophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 675 3-cyanophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 676 4-cyanophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 677 2-nitrophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 678 3-nitrophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 679 4-nitrophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 680 2-trifluoromethyl phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl -
[Table 2-5] Compound Nos. Q1 X1 X2 X3 X4 Q2 681 4-trifluoromethyl phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 682 4-trifluoromethoxy phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 683 2,3-difluorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 684 2,4-difluorophenyl F H H H 2, 6-dimethyl-4-(nonafluoro-2-butyl)phenyl 685 2,5-difluorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 686 2,6-difluorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 687 2,4-dichlorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 688 2,6-dichlorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 689 3,4-dichlorophenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-' butyl)phenyl 690 2-chloro-4-nitro phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 691 2-chloro-4-fluoro phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 692 2-chloro-6-fluoro phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 693 4-chloro-2-fluoro phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 694 4-chloro-2-nitro phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 695 2,3,6-trifluoro phenyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 696 pyridine-2-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 697 pyridine-3-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 698 2-fluoropyridine-3-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 699 2-chloropyridine-3-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 700 2-chloropyridine-5-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl -
[Table 2-6] Compound Nos. Q1 X1 X2 X3 X4 Q2 701 2-methylthio pyridine-3-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 702 pyrazine-2-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 703 furan-2-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 704 furan-3-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 705 2-tetrahydrofuranyl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 706 benzofuran-2-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 707 thiophene-2-yl F H H H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 708 phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 709 2-methylphenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 710 4-methylphenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 711 2-fluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 712 3-fluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 713 4-fluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 714 2-chlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 715 4-chlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 716 2-bromophenyl F. H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 717 2-iodophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 718 3-cyanophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 719 4-cyanophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 720 2-nitrophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 2-7] Compound Nos. Q1 X1 X2 X3 X4 Q2 721 3-nitrophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 722 4-nitrophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 723 2-trifluoromethyl phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 724 4-trifluoromethyl phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 725 4-trifluoromethoxy phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 726 2,3-difluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 727 2,4-difluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 728 2,5-difluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 729 2,6-difluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 730 2,4-dichlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 731 2,6-dichlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 732 3,4-dichlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 733 2-chloro-4-nitro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 734 2-chloro-4-fluoro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 735 2-chloro-6-fluoro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 736 4-chloro-2-fluoro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 737 4-chloro-2-nitro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 738 2,3,6-trifluoro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 739 pyridine-2-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 740 pyridine-3-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 2-8] Compound Nos. Q1 X1 X2 X3 X4 Q2 741 2-fluoropyridine-3-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 742 2-chloropyridine-3-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 793 2-chloropyridine-5-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 744 2-methylthio pyridine-3-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 745 pyrazine-2-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 746 furan-2-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 747 furan-3-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 748 2-tetrahydrofuranyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 749 benzofuran-2-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 750 thiophene-2-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 751 phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 752 2-methylphenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 753 4-methylphenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 754 2-fluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 755 3-fluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 756 4-fluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 757 2-chlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 758 4-chlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 759 2-bromophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 760 2-iodophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 2-9] Compound Nos. Q1 X1 X2 X3 X4 Q2 761 3-cyanophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 762 4-cyanophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 763 2-nitrophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 764 3-nitrophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 765 4-nitrophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 766 2-trifluoromethyl phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 767 4-trifluoromethyl phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 768 4-trifluoromethoxy phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 769 2,3-difluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 770 2,4-difluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 771 2,5-difluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 772 2,6-difluorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 773 2,4-dichlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 774 2,6-dichlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 775 3,4-dichlorophenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 776 2-chloro-4-nitro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 777 2-chloro-4-fluoro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 778 2-chloro-6-fluoro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 779 4-chloro-2-fluoro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 780 4-chloro-2-nitro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 2-10] Compound Nos. Q1 X1 X2 X3 X4 Q2 781 2,3,6-trifluoro phenyl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 782 pyridine-2-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 783 pyridine-3-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 784 2-fluoropyridine-3-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 785 2-chloropyridine-3-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 786 2-chloropyridine-5-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 787 2-methylthio pyridine-3-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 788 pyrazine-2-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 789 furan-2-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 790 thiophene-2-yl F H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 791 phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 792 2-methylphenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 793 4-methylphenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 794 2-fluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 795 3-fluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 796 4-fluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 797 2-chlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 798 4-chlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 799 2-bromophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 800 2-iodophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl -
[Table 2-11] Compound Nos. Q1 X1 X2 X3 X4 Q2 801 3-cyanophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 802 4-cyanophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 803 2-nitrophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 804 3-nitrophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 805 4-nitrophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 806 2-trifluoromethyl phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 807 4-trifluoromethyl phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 808 4-trifluoromethoxy phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 809 2,3-difluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 810 2,4-difluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 811 2,5-difluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 812 2,6-difluorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 813 2,4-dichlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 814 2,6-dichlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 815 3,4-dichlorophenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 816 2-chloro-4-nitro phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 817 2-chloro-4-fluoro phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 818 2-chloro-6-fluoro phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 819 4-chloro-2-fluoro phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 820 4-chloro-2-nitro phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl -
[Table 2-12] Compound Nos. Q1 X1 X2 X3 X4 Q2 821 2,3,6-trifluoro phenyl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 822 pyridine-2-yl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 823 pyridine-3-yl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 824 2-fluoropyridine-3-yl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 825 2-chloropyridine-3-yl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 826 2-chloropyridine-5-yl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 827 2-methylthio pyridine-3-yl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 828 pyrazine-2-yl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 829 furan-2-yl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 830 thiophene-2-yl F H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 831 phenyl Cl H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 832 2-fluorophenyl Cl H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 833 2-chloropyridine-3-yl Cl H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-1] Compound Nos. Q1 R1 R2 X1 X2 Q2 1001 phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1002 2-methylphenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1003 4-methylphenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1004 2-fluorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1005 3-fluorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1006 4-fluorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1007 2-chlorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1008 4-chlorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1009 2-bromophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1010 2-iodophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1011 3-cyanophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1012 4-cyanophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1013 2-nitrophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1014 3-nitrophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1015 4-nitrophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1016 2-trifluoromethyl phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1017 4-trifluoromethyl phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1018 4-trifluoromethoxy phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1019 2,3-difluorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1020 2,4-difluorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 3-2] Compound Nos. Q1 R1 R2 X1 X2 Q2 1021 2,5-difluorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1022 2,6-difluorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1023 2,4-dichlorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1024 2,6-dichlorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1025 3,4-dichlorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1026 2-chloro-4-nitro phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1027 2-chloro-4-fluoro phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1028 2-chloro-6-fluoro phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1029 4-chloro-2-fluoro phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1030 4-chloro-2-nitro phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1031 2,3,6-trifluoro phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1032 3-(acetylamino) phenyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1033 pyridine-2-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1034 pyridine-3-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1035 2-fluoropyridine-3-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1036 2-chloropyridine-3-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1037 2-chloropyridine-5-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1038 2-trifluoromethyl pyridine-3-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1039 2-methylthio pyridine-3-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1040 pyrazine-2-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 3-3] Compound Nos. Q1 R1 R2 X1 X2 Q2 1041 furan-2-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1042 furan-3-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1043 2-tetrahydrofuranyl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1044 benzofuran-2-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1045 thiophene-2-yl Me H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1046 phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1047 2-methylphenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1048 4-methylphenyl Me H H H 2-bromo-9-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1049 2-fluorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1050 3-fluorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1051 4-fluorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1052 2-chlorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1053 4-chlorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1054 2-bromophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1055 2-iodophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1056 3-cyanophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1057 4-cyanophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1058 2-nitrophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1059 3-nitrophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1060 4-nitrophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl -
[Table 3-4] Compound Nos. Q1 R1 R2 X1 X2 Q2 1061 2-trifluoromethyl phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1062 4-trifluoromethyl phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1063 4-trifluoromethoxy phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1064 2,3-difluorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1065 2,4-difluorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1066 2,5-difluorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1067 2,6-difluorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1068 2,4-dichlorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1069 2,6-dichlorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1070 3,4-dichlorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1071 2-chloro-4-nitro phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1072 2-chloro-4-fluoro phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1073 2-chloro-6-fluoro phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1074 4-chloro-2-fluoro phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1075 4-chloro-2-nitro phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1076 2,3,6-trifluoro phenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1077 pyridine-2-yl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1078 pyridine-3-yl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1079 2-fluoropyridine-3-yl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1080 2-chloropyridine-3-yl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl -
[Table 3-5] Compound Nos. Q1 R1 R2 X1 X2 Q2 1081 2-chloropyridine-5-yl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1082 2-methylthio pyridine-3-yl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1083 pyrazine-2-yl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1084 furan-2-yl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1085 thiophene-2-yl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfony)phenyl 1086 phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1087 2-methylphenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1088 4-methylphenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1089 2-fluorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1090 3-fluorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1091 4-fluorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1092 2-chlorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1093 4-chlorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1094 2-bromophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1095 2-iodophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1096 3-cyanophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1097 4-cyanophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1098 2-nitrophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1099 3-nitrophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1100 4-nitrophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl -
[Table 3-6] Compound Nos. Q1 R1 R2 X1 X2 Q2 1101 2-trifluoromethyl phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1102 4-trifluoromethyl phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1103 4-trifluoromethoxy phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1104 2,3-difluorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1105 2,4-difluorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1106 2,5-difluorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1107 2,6-difluorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1108 2,4-dichlorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1109 2,6-dichlorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1110 3,4-dichlorophenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1111 2-chloro-4-nitro phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1112 2-chloro-4-fluoro phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1113 2-chloro-6-fluoro phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1114 4-chloro-2-fluoro phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1115 4-chloro-2-nitro phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1116 2,3,6-trifluoro phenyl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1117 pyridine-2-yl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1118 pyridine-3-yl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1119 2-fluoropyridine-3-yl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1120 2-chloropyridine-3-yl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl -
[Table 3-7] Compound Nos. Q1 R1 R2 X1 X2 Q2 1121 2-chloropyridine-5-yl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1122 2-methylthio pyridine-3-yl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1123 pyrazine-2-yl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1124 furan-2-yl Me H H H 2-n-propyl-6-iodo-4-(hepta fluoroisopropyl)phenyl 1125 2-fluorophenyl Me H H H 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1126 phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1127 2-methylphenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1128 4-methylphenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1129 2-fluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1130 3-fluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1131 4-fluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1132 2-chlorophenyl Me H H H 2,6-dibromo-9-(heptafluoro-n-propylthio)phenyl 1133 4-chlorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1134 2-bromophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1135 2-iodophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1136 3-cyanophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1137 4-cyanophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1138 2-nitrophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1139 3-nitrophenyl Me H H H 2,6-dibromo-9-(heptafluoro-n-propylthio)phenyl 1140 4-nitrophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-8] Compound Nos. Q1 R1 R2 X1 X2 Q2 1141 2-trifluoromethyl phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1142 4-trifluoromethyl phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1143 4-trifluoromethoxy phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1144 2,3-difluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1145 2,4-difluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1146 2,5-difluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1147 2,6-difluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1148 2,4-dichlorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1149 2,6-dichlorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1150 3,4-dichlorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1151 2-chloro-4-nitro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1152 2-chloro-4-fluoro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1153 2-chloro-6-fluoro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1154 4-chloro-2-fluoro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1155 4-chloro-2-nitro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1156 2,3,6-trifluoro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1157 pyridine-2-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1158 pyridine-3-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1159 2-fluoropyridine-3-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1160 2-chloropyridine-3-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-9] Compound Nos. Q1 R1 R2 X1 X2 Q2 1161 2-chloropyridine-5-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1162 2-methylthio pyridine-3-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1163 pyrazine-2-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1164 furan-2-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1165 thiophene-2-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1166 phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1167 2-methylphenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1168 4-methylphenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1169 2-fluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1170 3-fluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1171 4-fluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1172 2-chlorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1173 4-chlorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1174 2-bromophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1175 2-iodophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1176 3-cyanophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1177 4-cyanophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1178 2-nitrophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1179 3-nitrophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1180 4-nitrophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 3-10] Compound Nos. Q1 R1 R2 X1 X2 Q2 1181 2-trifluoromethyl phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1182 4-trifluoromethyl phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1183 4-trifluoromethoxy phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1184 2,3-difluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1185 2,4-difluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1186 2,5-difluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1187 2,6-difluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1188 2,4-dichlorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1189 2,6-dichlorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1190 3,4-dichlorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1191 2-chloro-4-nitro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1192 2-chloro-4-fluoro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1193 2-chloro-6-fluoro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1194 4-chloro-2-fluoro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1195 4-chloro-2-nitro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1196 2,3,6-trifluoro phenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1197 pyridine-2-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1198 pyridine-3-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1199 2-fluoropyridine-3-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1200 2-chloropyridine-3-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 3-11] Compound Nos. Q1 R1 R2 X1 X2 Q2 1201 2-chloropyridine-5-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1202 2-methylthio pyridine-3-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1203 pyrazine-2-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1204 furan-2-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1205 thiophene-2-yl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1206 2-fluorophenyl Et H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1207 pyridine-3-yl Et H H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1208 phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1209 2-methylphenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1210 3-methylphenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1211 4-methylphenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1212 2-nitrophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1213 3-nitrophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1214 4-nitrophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1215 2-cyanophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1216 3-cyanophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1217 4-cyanophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1218 2-fluorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1219 3-fluorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1220 4-fluorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 3-12] Compound Nos. Q1 R1 R2 X1 X2 Q2 1221 2-chlorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1222 4-chlorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1223 2-bromophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1224 2-iodophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1225 2-trifluoromethyl phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1226 4-trifluoromethyl phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1227 4-trifluoromethoxy phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1228 2,3-difluorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1229 2,4-difluorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1230 2,5-difluorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1231 2,6-difluorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1232 2,4-dichlorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1233 2,6-dichlorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1234 3,4-dichlorophenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1235 2-fluoro-4-nitro phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1236 4-fluoro-2-nitro phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1237 2-chloro-4-fluoro phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1238 4-chloro-2-fluoro phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1239 2-chloro-6-fluoro phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1240 2-chloro-4-nitro phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 3-13] Compound Nos. Q1 R1 R2 X1 X2 Q2 1241 4-chloro-2-nitro phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1242 2,3,6-trifluoro phenyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1243 pyridine-2-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1244 pyridine-3-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1245 2-chloropyridine-3-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1246 2-fluoropyridine-3-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1247 2-chloropyridine-5-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1248 2-methylthio pyridine-3-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1249 pyrazine-2-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1250 furan-2-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1251 furan-3-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1252 2-tetrahydrofuranyl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1253 benzofuran-2-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1254 thiophene-2-yl Me H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1255 phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1256 2-methylphenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1257 3-methylphenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1258 4-methylphenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1259 2-nitrophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1260 3-nitrophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl -
[Table 3-14] Compound Nos. Q1 R1 R2 X1 X2 Q2 1261 4-nitrophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1262 2-cyanophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1263 3-cyanophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1264 4-cyanophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1265 2-fluorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1266 3-fluorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1267 4-fluorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1268 2-chlorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1269 4-chlorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1270 2-bromophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1271 2-iodophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1272 2-trifluoromethyl phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1273 4-trifluoromethyl phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1274 4-trifluoromethoxy phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1275 2,3-difluorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1276 2,4-difluorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1277 2,5-difluorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1278 2,6-difluorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1279 2,4-dichlorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1280 2,6-dichlorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl -
[Table 3-15] Compound Nos. Q1 R1 R2 X1 X2 Q2 1281 3,4-dichlorophenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1282 2-fluoro-4-nitro phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1283 4-fluoro-2-nitro phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1284 2-chloro-4-fluoro phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1285 4-chloro-2-fluoro phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1286 2-chloro-6-fluoro phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1287 2-chloro-4-nitro phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1288 4-chloro-2-nitro phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1289 2,3,6-trifluoro phenyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1290 pyridine-2-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1291 pyridine-3-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1292 2-fluoropyridine-3-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1293 2-chloropyridine-3-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1294 2-chloropyridine-5-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1295 2-methylthio pyridine-3-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1296 pyrazine-2-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1297 furan-2-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1298 furan-3-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1299 2-tetrahydrofuranyl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1300 benzofuran-2-yl Me H F H 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl -
[Table 3-16] Compound Nos. Q1 R1 R2 X1 X2 Q2 1301 thiophene-2-yl Me H F H 2, 6-dimethyl-4- (nonafluoro-2-butyl)phenyl 1302 phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1303 2-methylphenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1304 4-methylphenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1305 2-fluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1306 3-fluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1307 4-fluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1308 2-chlorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1309 4-chlorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1310 2-bromophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1311 2-iodophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1312 3-cyanophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1313 4-cyanophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1314 2-nitrophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1315 3-nitrophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1316 4-nitrophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1317 2-trifluoromethyl phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1318 4-trifluoromethyl phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1319 4-trifluoromethoxy phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1320 2,3-difluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl -
[Table 3-17] Compound Nos. Q1 R1 R2 X1 X2 Q2 1321 2,4-difluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1322 2,5-difluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1323 2,6-difluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1324 2,4-dichlorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1325 2,6-dichlorophenyl Me H F H 2-bromo-4- (heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1326 3,4-dichlorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1327 2-chloro-4-nitro phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1328 2-chloro-4-fluoro phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1329 2-chloro-6-fluoro phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1330 4-chloro-2-fluoro phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1331 4-chloro-2-nitro phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1332 2,3,6-trifluoro phenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1333 pyridine-2-yl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1334 pyridine-3-yl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1335 2-fluoropyridine-3-yl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1336 2-chloropyridine-3-yl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1337 2-chloropyridine-5-yl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1338 2-methylthio pyridine-3-yl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1339 pyrazine-2-yl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1340 furan-2-yl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl -
[Table 3-18] Compound Nos. Q1 R1 R2 X1 X2 Q2 1341 thiophene-2-yl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1342 phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1343 2-methylphenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1344 4-methylphenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1345 2-fluorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1346 3-fluorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1347' 4-fluorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1348 2-chlorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1349 4-chlorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl) phenyl 1350 2-bromophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1351 2-iodophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1352 3-cyanophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1353 4-cyanophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1354 2-nitrophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1355 3-nitrophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1356 4-nitrophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1357 2-trifluoromethyl phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1358 4-trifluoromethyl phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1359 4-trifluoromethoxy phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1360 2,3-difluorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl -
[Table 3-19] Compound Nos. Q1 R1 R2 X1 X2 Q2 1361 2,4-difluorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1362 2,5-difluorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1363 2,6-difluorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1364 2,4-dichlorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1365 2,6-dichlorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1366 3,4-dichlorophenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1367 2-chloro-4-nitro phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1368 2-chloro-4-fluoro phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1369 2-chloro-6-fluoro phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1370 4-chloro-2-fluoro phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1371 4-chloro-2-nitro phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1372 2,3,6-trifluoro phenyl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1373 pyridine-2-yl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1374 pyridine-3-yl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1375 2-fluoropyridine-3-yl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1376 2-chloropyridine--yl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1377 2-chloropyridine-5-yl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1378 2-methylthio pyridine-3-yl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1379 pyrazine-2-yl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1380 furan-2-yl Me H F H 2-n-propyl-6-iodo-9-(heptafluoro isopropyl)phenyl -
[Table 3-20] Compound Nos. Q1 R1 R2 X1 X2 Q2 1381 thiophene-2-yl Me H F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1382 phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1383 2-methylphenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1384 4-methylphenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1385 2-fluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1386 3-fluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1387 4-fluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1388 2-chlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1389 4-chlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1390 2-bromophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1391 2-iodophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1392 3-cyanophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1393 4-cyanophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1394 2-nitrophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1395 3-nitrophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1396 4-nitrophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1397 2-trifluoromethyl phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1398 4-trifluoromethyl phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1399 4-trifluoromethoxy phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1400 2,3-difluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-21] Compound Nos. Q1 R1 R2 X1 X2 Q2 1401 2,4-difluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1402 2,5-difluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1403 2,6-difluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1404 2,4-dichlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1405 2,6-dichlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1406 3,4-dichlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1407 2-chloro-4-nitro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1408 2-chloro-4-fluoro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1409 2-chloro-6-fluoro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1410 4-chloro-2-fluoro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1411 4-chloro-2-nitro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1412 2,3,6-trifluoro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1413 pyridine-2-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1414 pyridine-3-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1415 2-fluoropyridine-3-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1416 2-chloropyridine-3-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1417 2-chloropyridine-5-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1418 2-methylthio pyridine-3-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1419 pyrazine-2-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1420 furan-2-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-22] Compound Nos. Q1 R1 R2 X1 X2 Q2 1421 thiophene-2-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1422 phenyl Me H F H 2, 6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1423 2-methylphenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1424 4-methylphenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1425 2-fluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1426 3-fluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1427 4-fluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1428 2-chlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1429 4-chlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1430 2-bromophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1431 2-iodophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1432 3-cyanophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1433 4-cyanophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1434 2-nitrophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1435 3-nitrophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1436 4-nitrophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1437 2-trifluoromethyl phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1438 4-trifluoromethyl phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1439 4-trifluoromethoxy phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1440 2,3-difluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 3-23] Compound Nos. Q1 R1 R2 X1 X2 Q2 1441 2,4-difluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1442 2,5-difluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1443 2,6-difluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1444 2,4-dichlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1445 2,6-dichlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1446 3,4-dichlorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1447 2-chloro-4-nitro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1448 2-chloro-4-fluoro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1449 2-chloro-6-fluoro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1450 4-chloro-2-fluoro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1451 4-chloro-2-nitro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1452 2,3,6-trifluoro phenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1453 pyridine-2-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1454 pyridine-3-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1455 2-fluoropyridine-3-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1456 2-chloropyridine-3-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1457 2-chloropyridine-5-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1458 2-methylthio pyridine-3-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1459 pyrazine-2-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1460 furan-2-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 3-24] Compound Nos. Q1 R1 R2 X1 X2 Q2 1461 thiophene-2-yl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1462 phenyl Et H F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1463 phenyl Me H H F 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1464 4-nitrophenyl Me H H F 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1465 4-cyanophenyl Me H H F 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1466 phenyl Me H H F 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1467 4-nitrophenyl Me H H F 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1468 4-cyanophenyl Me H H F 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1469 phenyl Me H H F 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1470 4-nitrophenyl Me H H F 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1471 4-cyanophenyl Me H H F 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1472 phenyl Me H H F 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1473 4-nitrophenyl Me H H F 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1474 4-cyanophenyl Me H H F 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1475 phenyl Me H H F 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 1476 4-nitrophenyl Me H H F 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 1477 4-cyanophenyl Me H H F 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 1478 phenyl H Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1479 phenyl H Me H H 2-bromo-4-(heptafluoroisopropyl)--methyphenyl 1480 phenyl H Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-25] Compound Nos. Q1 R1 R2 X1 X2 Q2 1481 2-fluorophenyl H Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1482 phenyl H Et H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1483 phenyl H i-Pr H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1484 phenyl H acetyl H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1485 phenyl H Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1486 2-fluorophenyl H Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1487 phenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1488 2-methylphenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1489 4-methylphenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1490 2-fluorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1491 3-fluorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1492 4-fluorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1493 2-chlorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1494 4-chlorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1495 2-bromophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1496 2-iodophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1497 3-cyanophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1498 4-cyanophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1499 2-nitrophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1500 3-nitrophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 3-26] Compound Nos. Q1 R1 R2 X1 X2 Q2 1501 4-nitrophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1502 2-trifluoromethyl phenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1503 4-trifluoromethyl phenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1504 4-trifluoromethoxy phenyl Me Me H H 2,6-dimethyl-9-(heptafluoro isopropyl)phenyl 1505 2,3-difluorophenyl Me Me H H 2,6-dimethyl-9-(heptafluoro isopropyl)phenyl 1506 2,4-difluorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1507 2,5-difluorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1508 2,6-difluorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1509 2,4-dichlorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1510 2,6-dichlorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1511 3,4-dichlorophenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1512 2-chloro-4-nitro phenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1513 2-chloro-4-fluoro phenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1514 2-chloro-6-fluoro phenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1515 4-chloro-2-fluoro phenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1516 4-chloro-2-nitro phenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1517 2,3,6-trifluoro phenyl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1518 pyridine-2-yl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1519 pyridine-3-yl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1520 2-fluoropyridine-3-yl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 3-27] Compound Nos. Q1 R1 R2 X1 X2 Q2 1521 2-chloropyridine-3-yl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1522 2-chloropyridine-5-yl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1523 2-methylthio pyridine-3-yl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1524 pyrazine-2-yl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1525 furan-2-yl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1526 , thiophene-2-yl Me Me H H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1527 phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1528 2-methylphenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1529 4-methylphenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1530 2-fluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1531 3-fluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1532 4-fluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1533 2-chlorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1534 4-chlorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1535 2-bromophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1536 2-iodophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1537 3-cyanophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1538 4-cyanophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1539 2-nitrophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1540 3-nitrophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl -
[Table 3-28] Compound Nos. Q1 R1 R2 X1 X2 Q2 1541 4-nitrophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1542 2-trifluoromethyl phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1543 4-trifluoromethyl phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1544 4-trifluoromethoxy phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1545 2,3-difluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1546 2,4-difluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1547 2,5-difluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1548 2,6-difluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1549 2,4-dichlorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1550 2,6-dichlorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1551 3,4-dichlorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1552 2-chloro-4-nitro phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1553 2-chloro-4-fluoro phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1554 2-chloro-6-fluoro phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1555 4-chloro-2-fluoro phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1556 4-chloro-2-nitro phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1557 2,3,6-trifluoro phenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1558 pyridine-2-yl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1559 pyridine-3-yl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1560 2-fluoropyridine-3-yl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl -
[Table 3-29] Compound Nos. Q1 R1 R2 X1 X2 Q2 1561 2-chloropyridine-3-yl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1562 2-chloropyridine-5-yl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1563 2-methylthio pyridine-3-yl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1564 pyrazine-2-yl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1565 furan-2-yl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1566 thiophene-2-yl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1567 phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1568 2-methylphenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1569 4-methylphenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1570 2-fluorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1571 3-fluorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1572 4-fluorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1573 2-chlorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1574 4-chlorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1575 2-bromophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1576 2-iodophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1577 3-cyanophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1578 4-cyanophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1579 2-nitrophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1580 3-nitrophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl -
[Table 3-30] Compound Nos. Q1 R1 R2 X1 X2 Q2 1581 4-nitrophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl) phenyl 1582 2-trifluoromethyl phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1583 4-trifluoromethyl phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1584 4-trifluoromethoxy phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1585 2,3-difluorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1586 2,4-difluorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1587 2,5-difluorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1588 2,6-difluorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1589 2,4-dichlorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1590 2,6-dichlorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1591 3,4-dichlorophenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1592 2-chloro-4-nitro phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1593 2-chloro-4-fluoro phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1594 2-chloro-6-fluoro phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1595 4-chloro-2-fluoro phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1596 4-chloro-2-nitro phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1597 2,3,6-trifluoro phenyl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1598 pyridine-2-yl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1599 pyridine-3-yl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1600 2-fluoropyridine-3-yl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl -
[Table 3-31] Compound Nos. Q1 R1 R2 X1 X2 Q2 1601 2-chloropyridine-3-yl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1602 2-chloropyridine-5-yl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1603 2-methylthio pyridine-3-yl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1604 pyrazine-2-yl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1605 furan-2-yl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1606 thiophene-2-yl Me Me H H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1607 phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1608 2-methylphenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1609 3-methylphenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1610 4-methylphenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1611 2-nitrophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1612 3-nitrophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1613 4-nitrophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1614 2-cyanophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1615 3-cyanophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1616 4-cyanophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1617 2-fluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1618 3-fluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1619 4-fluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1620 2-chlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-32] Compound Nos. Q1 R1 R2 X1 X2 Q2 1621 4-chlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1622 2-bromophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1623 2-iodophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1624 2-trifluoromethyl phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1625 4-trifluoromethyl phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1626 4-trifluoromethoxy phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1627 2,3-difluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1628 2,4-difluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1629 2,5-difluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1630 2,6-difluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1631 2,4-dichlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1632 2,6-dichlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1633 3,4-dichlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1634 2-fluoro-4-nitro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1635 4-fluoro-2-nitro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1636 2-chloro-4-fluoro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1637 4-chloro-2-fluoro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1638 2-chloro-6-fluoro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1639 2-chloro-4-nitro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1640 4-chloro-2-nitro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-33] Compound Nos. Q1 R1 R2 X1 X2 Q2 1641 2,3,6-trifluoro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1642 pyridine-2-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1643 pyridine-3-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1644 2-fluoropyridine-3-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1645 2-chloropyridine-3-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1646 2-chloropyridine-5-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1647 2-methylthio pyridine-3-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1648 pyrazine-2-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1649 furan-2-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1650 furan-3-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1651 2-tetrahydrofuranyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1652 benzofuran-2-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1653 thiophene-2-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1654 3,4-dinitrophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1655 3-methoxy-4-nitro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1656 2,3,4-trifluoro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1657 phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1658 2-methylphenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1659 4-methylphenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1660 2-fluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 3-34] Compound Nos. Q1 R1 R2 X1 X2 Q2 1661 3-fluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1662 4-fluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1663 2-chlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1664 4-chlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1665 2-bromophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1666 2-iodophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1667 3-cyanophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1668 4-cyanophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1669 2-nitrophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1670 3-nitrophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1671 4-nitrophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1672 2-trifluoromethyl phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1673 4-trifluoromethyl phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1674 4-trifluoromethoxy phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1675 2,3-difluorophenyl Me Me H H 2,6-dibromo-9-(heptafluoro-n-propylsulfinyl)phenyl 1676 2,4-difluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1677 2,5-difluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1678 2,6-difluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1679 2,4-dichlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1680 2,6-dichlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 3-35] Compound Nos. Q1 R1 R2 X1 X2 Q2 1681 3,4-dichlorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1682 2-chloro-4-nitro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1683 2-chloro-4-fluoro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1684 2-chloro-6-fluoro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1685 4-chloro-2-fluoro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1686 4-chloro-2-nitro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1687 2,3,6-trifluoro phenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1688 pyridine-2-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1689 pyridine-3-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1690 2-fluoropyridine-3-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1691 2-chloropyridine-3-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1692 2-chloropyridine-5-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1693 2-methylthio pyridine-3-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1694 pyrazine-2-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1695 furan-2-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1696 thiophene-2-yl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1697 phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1698 2-methylphenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1699 4-methylphenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1700 2-fluorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 3-36] Compound Nos. Q1 R1 R2 X1 X2 Q2 1701 3-fluorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1702 4-fluorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1703 2-chlorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1704 4-chlorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1705 2-bromophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1706 2-iodophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1707 3-cyanophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1708 4-cyanophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1709 2-nitrophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1710 3-nitrophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1711 4-nitrophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1712 2-trifluoromethyl phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1713 4-trifluoromethyl phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1714 4-trifluoromethoxy phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1715 2,3-difluorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1716 2,4-difluorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1717 2,5-difluorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1718 2,6-difluorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1719 2,4-dichlorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1720 2,6-dichlorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl -
[Table 3-37] Compound Nos. Q1 R1 R2 X1 X2 Q2 1721 3,4-dichlorophenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1722 2-chloro-4-nitro phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1723 2-chloro-4-fluoro phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1724 2-chloro-6-fluoro phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1725 4-chloro-2-fluoro phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1726 4-chloro-2-nitro phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1727 2,3,6-trifluoro phenyl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1728 pyridine-2-yl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1729 pyridine-3-yl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1730 2-fluoropyridine-3-yl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1731 2-chloropyridine-3-yl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl) phenyl 1732 2-chloropyridine-5-yl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1733 2-methylthio pyridine-3-yl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1734 pyrazine-2-yl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1735 furan-2-yl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1736 thiophene-2-yl Me Me F H 2,6-dimethyl-4-(heptafluoro isopropyl)phenyl 1737 phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1738 2-methylphenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1739 4-methylphenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1740 2-fluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl -
[Table 3-38] Compound Nos. Q1 R1 R2 X1 X2 Q2 1741 3-fluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1742 4-fluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1743 2-chlorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1744 4-chlorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1745 2-bromophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1746 2-iodophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1747 3-cyanophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1748 4-cyanophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1749 2-nitrophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1750 3-nitrophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1751 4-nitrophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1752 2-trifluoromethyl phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1753 4-trifluoromethyl phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1754 4-trifluoromethoxy phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1755 2,3-difluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1756 2,4-difluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1757 2,5-difluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1758 2,6-difluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1759 2,4-dichlorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1760 2,6-dichlorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl -
[Table 3-39] Compound Nos. Q1 R1 R2 X1 X2 Q2 1761 3,4-dichlorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1762 2-chloro-4-nitro phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1763 2-chloro-4-fluoro phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1764 2-chloro-6-fluoro phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1765 4-chloro-2-fluoro phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1766 4-chloro-2-nitro phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1767 2,3,6-trifluoro phenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1768 pyridine-2-yl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1769 pyridine-3-yl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1770 2-fluoropyridine-3-yl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1771 2-chloropyridine-3-yl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1772 2-chloropyridine-5-yl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1773 2-methylthio pyridine-3-yl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1774 pyrazine-2-yl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1775 furan-2-yl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1776 thiophene-2-yl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl 1777 phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1778 2-methylphenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1779 4-methylphenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1780 2-fluorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl -
[Table 3-40] Compound Nos. Q1 R1 R2 X1 X2 Q2 1781 3-fluorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1782 4-fluorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1783 2-chlorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1784 4-chlorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1785 2-bromophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1786 2-iodophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1787 3-cyanophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1788 4-cyanophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1789 2-nitrophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1790 3-nitrophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1791 4-nitrophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1792 2-trifluoromethyl phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1793 4-trifluoromethyl phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1794 4-trifluoromethoxy phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1795 2,3-difluorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1796 2,4-difluorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1797 2,5-difluorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1798 2,6-difluorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1799 2,4-dichlorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1800 2,6-dichlorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl -
[Table 3-41] Compound Nos. Q1 R1 R2 X1 X2 Q2 1801 3,4-dichlorophenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1802 2-chloro-4-nitro phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1803 2-chloro-4-fluoro phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1804 2-chloro-6-fluoro phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1805 4-chloro-2-fluoro phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1806 4-chloro-2-nitro phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1807 2,3,6-trifluoro phenyl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1808 pyridine-2-yl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1809 pyridine-3-yl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1810 2-fluoropyridine-3-yl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1811 2-chloropyridine-3-yl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1812 2-chloropyridine-5-yl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1813 2-methylthio pyridine-3-yl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1814 pyrazine-2-yl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1815 furan-2-yl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1816 thiophene-2-yl Me Me F H 2-n-propyl-6-iodo-4-(heptafluoro isopropyl)phenyl 1817 phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1818 2-methylphenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1819 4-methylphenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1820 2-fluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-42] Compound Nos. Q1 R1 R2 X1 X2 Q2 1821 3-fluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1822 4-fluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1823 2-chlorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1824 4-chlorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1825 2-bromophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1826 2-iodophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1827 3-cyanophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1828 4-cyanophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1829 2-nitrophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1830 3-nitrophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1831 4-nitrophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1832 2-trifluoromethyl phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1833 4-trifluoromethyl phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1834 4-trifluoromethoxy phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1835 2,3-difluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1836 2,4-difluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1837 2,5-difluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1838 2,6-difluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1839 2,4-dichlorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1840 2,6-dichlorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 3-43] Compound Nos. Q1 R1 R2 X1 X2 Q2 1841 3,4-dichlorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1842 2-chloro-4-nitro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1843 2-chloro-4-fluoro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1844 2-chloro-6-fluoro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1845 4-chloro-2-fluoro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1846 4-chloro-2-nitro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1847 2,3,6-trifluoro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1848 pyridine-2-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1849 pyridine-3-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1850 2-fluoropyridine-3-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1851 2-chloropyridine-3-yl Me Me F H 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1852 2-chloropyridine-5-yl Me Me F H 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1853 2-methylthio pyridine-3-yl Me Me F H 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1854 pyrazine-2-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1855 furan-2-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1856 thiophene-2-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1857 phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1858 2-methylphenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1859 4-methylphenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1860 2-fluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 3-44] Compound Nos. Q1 R1 R2 X1 X2 Q2 1861 3-fluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1862 4-fluorophenyl Me Me F H 2,6-dibromo-9-(heptafluoro-n-propylsulfinyl)phenyl 1863 2-chlorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1864 4-chlorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1865 2-bromophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1866 2-iodophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1867 3-cyanophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1868 4-cyanophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1869 2-nitrophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1870 3-nitrophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1871 4-nitrophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1872 2-trifluoromethyl phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1873 4-trifluoromethyl phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1874 4-trifluoromethoxy phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1875 2,3-difluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1876 2,4-difluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1877 2,5-difluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1878 2,6-difluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1879 2,4-dichlorophenyl Me Me F H 2,6-dibromo-9-(heptafluoro-n-propylsulfinyl)phenyl 1880 2,6-dichlorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl -
[Table 3-45] Compound Nos. Q1 R1 R2 X1 X2 Q2 1881 3,4-dichlorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1882 2-chloro-4-nitro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1883 2-chloro-4-fluoro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1884 2-chloro-6-fluoro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1885 4-chloro-2-fluoro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1886 4-chloro-2-nitro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1887 2,3,6-trifluoro phenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1888 pyridine-2-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1889 pyridine-3-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1890 2-fluoropyridine-3-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1891 2-chloropyridine-3-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1892 2-chloropyridine-5-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1893 2-methylthio pyridine-3-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1894 pyrazine-2-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1895 furan-2-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1896 thiophene-2-yl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 1897 2-fluorophenyl Me H H H 2,6-dibromo-4-(pentafluoroethyl) phenyl 1898 2-fluorophenyl Me H H H 2-bromo-4-(heptafluoro isopropyl)-6-methylphenyl 1899 2-fluorophenyl Me H H H 2-ethyl-4-(heptafluoro isopropyl)-6-methylphenyl 1900 2-fluorophenyl Me H H H 4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl -
[Table 3-46] Compound Nos. Q1 R1 R2 X1 X2 Q2 1901 2-fluorophenyl Me H H H 2-chloro-6-ethyl-4-(heptafluoro isopropyl)phenyl 1902 2-fluorophenyl Me H H H 2-bromo-6-ethyl-4-(heptafluoro isopropyl)phenyl 1903 2-fluorophenyl Me H H H 2-ethyl-4-(heptafluoro isopropyl)-6-iodophenyl 1904 2-fluorophenyl Me H H H 4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl 1905 2-fluorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl 1906 2-fluorophenyl Me H H H 2-bromo-4-(heptafluoroisopropyl)-6-(trifluoromethylthio)phenyl 1907 2-fluorophenyl Me H H H 2,6-dibromo-4-(trifluoro methylthio)phenyl 1908 2-fluorophenyl Me H H H 2,6-dibromo-4-(pentafluoro ethylthio)phenyl 1909 2-fluorophenyl Me H H H 2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl 1910 2-fluorophenyl Me H H H 2,6-dichloro-4-(heptafluoro isopropylsulfonyl)phenyl 1911 2-fluorophenyl Me H H H 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 1912 2-fluorophenyl Me H H H 2-bromo-6-(heptafluoroisopropyl oxy)-4-methylpyridine-3-yl 1913 2-fluorophenyl Me H H H 2,4-dimethyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-yl 1914 2-fluorophenyl Me H H H 2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1915 2-fluorophenyl Me H H H 2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1916 2-fluorophenyl Me H H H 2-iodo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1917 2-fluorophenyl Me H F H 2,6-dibromo-4-(pentafluoro ethyl)phenyl 1918 2-fluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-methylphenyl 1919 2-fluorophenyl Me H F H 2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl 1920 2-fluorophenyl Me H F H 4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl -
[Table 3-47] Compound Nos. Q1 R1 R2 X1 X2 Q2 1921 2-fluorophenyl Me H F H 2-chloro-6-ethyl-4-(heptafluoro isopropyl)phenyl 1922 2-fluorophenyl Me H F H 2-bromo-6-ethyl-4-(heptafluoro isopropyl)phenyl 1923 2-fluorophenyl Me H F H 2-ethyl-4-(heptafluoro isopropyl)-6-iodophenyl 1924 2-fluorophenyl Me H F H 4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl 1925 2-fluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl 1926 2-fluorophenyl Me H F H 2-bromo-4-(heptafluoroisopropyl)-6-(trifluoromethylthio)phenyl 1927 2-fluorophenyl Me H F H 2,6-dibromo-4-(trifluoro methylthio)phenyl 1928 2-fluorophenyl Me H F H 2,6-dibromo-4-(pentafluoro ethylthio)phenyl 1929 2-fluorophenyl Me H F H 2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl 1930 2-fluorophenyl Me H F H 2,6-dichloro-4-(heptafluoro isopropylsulfonyl)phenyl 1931 2-fluorophenyl Me H F H 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 1932 2-fluorophenyl Me H F H 2-bromo-6-(heptafluoroisopropyl oxy)-4-methylpyridine-3-yl 1933 2-fluorophenyl Me H F H 2,4-dimethyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl 1934 2-fluorophenyl Me H F H 2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1935 2-fluorophenyl Me H F H 2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1936 2-fluorophenyl Me H F H 2-iodo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1937 2-fluorophenyl Me Me H H 2,6-dibromo-4-(pentafluoro ethyl)phenyl 1938 2-fluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-methylphenyl 1939 2-fluorophenyl Me Me H H 2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl 1940 2-fluorophenyl Me Me H H 4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl -
[Table 3-48] Compound Nos. Q1 R1 R2 X1 X2 Q2 1941 2-fluorophenyl Me Me H H 2-chloro-6-ethyl-4-(heptafluoro isopropyl)phenyl 1942 2-fluorophenyl Me Me H H 2-bromo-6-ethyl-4-(heptafluoro isopropyl)phenyl 1943 2-fluorophenyl Me Me H H 2-ethyl-4-(heptafluoro isopropyl)-6-iodophenyl 1944 2-fluorophenyl Me Me H H 4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl 1945 2-fluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl 1946 2-fluorophenyl Me Me H H 2-bromo-4-(heptafluoroisopropyl)-6-(trifluoromethylthio)phenyl 1947 2-fluorophenyl Me Me H H 2,6-dibromo-4-(trifluoro methylthio)phenyl 1948 2-fluorophenyl Me Me H H 2,6-dibromo-4-(pentafluoro ethylthio)phenyl 1949 2-fluorophenyl Me Me H H 2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl 1950 2-fluorophenyl Me Me H H 2,6-dichloro-4-(heptafluoro isopropylsulfonyl)phenyl 1951 2-fluorophenyl Me Me H H 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 1952 2-fluorophenyl Me Me H H 2-bromo-6-(heptafluoroisopropyl oxy)-4-methylpyridine-3-yl 1953 2-fluorophenyl Me Me H H 2,4-dimethyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl 1954 2-fluorophenyl Me Me H H 2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1955 2-fluorophenyl Me Me H H 2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1956 2-fluorophenyl Me Me H H 2-iodo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1957 2-fluorophenyl Me Me F H 2,6-dibromo-4-(pentafluoro ethyl)phenyl 1958 2-fluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-methylphenyl 1959 2-fluorophenyl Me Me F H 2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl 1960 2-fluorophenyl Me Me F H 4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl -
[Table 3-49] Compound Nos. Q1 R1 R2 X1 X2 Q2 1961 2-fluorophenyl Me Me F H 2-chloro-6-ethyl-4-(heptafluoro isopropyl)phenyl 1962 2-fluorophenyl Me Me F H 2-bromo-6-ethyl-4-(heptafluoro isopropyl)phenyl 1963 2-fluorophenyl Me Me F H 2-ethyl-4-(heptafluoro isopropyl)-6-iodophenyl 1964 2-fluorophenyl Me Me F H 4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl 1965 2-fluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl 1966 2-fluorophenyl Me Me F H 2-bromo-4-(heptafluoroisopropyl)-6-(trifluoromethylthio)phenyl 1967 2-fluorophenyl Me Me F H 2,6-dibromo-4-(trifluoro methylthio)phenyl 1968 2-fluorophenyl Me Me F H 2,6-dibromo-4-(pentafluoro ethylthio)phenyl 1969 2-fluorophenyl Me Me F H 2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl 1970 2-fluorophenyl Me Me F H 2,6-dichloro-4-(heptafluoro isopropylsulfonyl)phenyl 1971 2-fluorophenyl Me Me F H 2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl 1972 2-fluorophenyl Me Me F H 2-bromo-6-(heptafluoroisopropyl oxy)-4-methylpyridine-3-yl 1973 2-fluorophenyl Me Me F H 2,4-dimethyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl 1974 2-fluorophenyl Me Me F H 2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1975 2-fluorophenyl Me Me F H 2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl 1976 2-fluorophenyl Me Me F H 2-iodo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethyl ethoxy)pyridine-3-yl -
[Table 4-1] Compound Nos. Q1 R1 A1 A2 Q2 2001 phenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2002 2-methylphenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2003 4-methylphenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2004 2-fluorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2005 3-fluorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2006 4-fluorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2007 2-chlorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2008 4-chlorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2009 2-bromophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2010 2-iodophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2011 3-cyanophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2012 4-cyanophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2013 2-nitrophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2014 3-nitrophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2015 4-nitrophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2016 2-trifluoromethyl phenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2017 4-trifluoromethyl phenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2018 4-trifluoromethoxy phenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2019 2,3-difluorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2020 2,4-difluorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl -
[Table 4-2] Compound Nos. Q1 R1 A1 A2 Q2 2021 2,5-difluorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2022 2,6-difluorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2023 2,4-dichlorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2024 2,6-dichlorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2025 3,4-dichlorophenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2026 2-chloro-4-nitro phenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2027 2-chloro-4-fluoro phenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2028 2-chloro-6-fluoro phenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2029 4-chloro-2-fluoro phenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2030 4-chloro-2-nitro phenyl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2031 2,3,6-trifluoro phenyl H N C 2,6-dimethyl-9-heptafluoro isopropylphenyl 2032 pyridine-2-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2033 pyridine-3-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2034 pyridine-4-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2035 2-fluoropyridine-3-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2036 2-chloropyridine-3-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2037 2-chloropyridine-5-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2038 2-methylthio pyridine-3-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2039 pyrazine-2-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2040 furan-2-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl -
[Table 4-3] Compound Nos. Q1 R1 A1 A2 Q2 2041 thiophene-2-yl H N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2042 phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2043 2-methylphenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2044 4-methylphenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2045 2-fluorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2046 3-fluorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2047 4-fluorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2048 2-chlorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2049 4-chlorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2050 2-bromophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2051 2-iodophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2052 3-cyanophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2053 4-cyanophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2054 2-nitrophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2055 3-nitrophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2056 4-nitrophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2057 2-trifluoromethyl phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2058 4-trifluoromethyl phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2059 4-trifluoromethoxy phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2060 2,3-difluorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 4-4] Compound Nos. Q1 R1 A1 A2 Q2 2061 2,4-difluorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2062 2,5-difluorophenyl H N C 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2063 2,6-difluorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2064 2,4-dichlorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2065 2,6-dichlorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2066 3,4-dichlorophenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2067 2-chloro-4-nitro phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2068 2-chloro-4-fluoro phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2069 2-chloro-6-fluoro phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2070 4-chloro-2-fluoro phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2071 4-chloro-2-nitro phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2072 2,3,6-trifluoro phenyl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2073 pyridine-2-yl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2074 pyridine-3-yl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2075 2-fluoropyridine-3-yl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2076 2-chloropyridine-3-yl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2077 2-chloropyridine-5-yl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2078 2-methylthio pyridine-3-yl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2079 pyrazine-2-yl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2080 furan-2-yl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 4-5] Compound Nos. Q1 R1 A1 A2 Q2 2081 thiophene-2-yl H N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2082 phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2083 2-methylphenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2084 4-methylphenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2085 2-fluorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2086 3-fluorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2087 4-fluorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2088 2-chlorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2089 4-chlorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2090 2-bromophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2091 2-iodophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2092 3-cyanophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2093 4-cyanophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2094 2-nitrophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2095 3-nitrophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2096 4-nitrophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2097 2-trifluoromethyl phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2098 4-trifluoromethyl phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2099 4-trifluoromethoxy phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2100 2,3-difluorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl -
[Table 4-6] Compound Nos. Q1 R1 A1 A2 Q2 2101 2,4-difluorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2102 2,5-difluorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2103 2,6-difluorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2104 2,4-dichlorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2105 2,6-dichlorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2106 3,4-dichlorophenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2107 2-chloro-4-nitro phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2108 2-chloro-4-fluoro phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2109 2-chloro-6-fluoro phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2110 4-chloro-2-fluoro phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2111 4-chloro-2-nitro phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2112 2,3,6-trifluoro phenyl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2113 pyridine-2-yl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2114 pyridine-3-yl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2115 2-fluoropyridine-3-yl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2116 2-chloropyridine-3-yl Me N C 2, 6-dimethyl-4-heptafluoro isopropylphenyl 2117 2-chloropyridine-5-yl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2118 2-methylthio pyridine-3-yl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2119 pyrazine-2-yl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2120 furan-2-yl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl -
[Table 4-7] Compound Nos. Q1 R1 A1 A2 Q2 2121 thiophene-2-yl Me N C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2122 phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2123 2-methylphenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2124 4-methylphenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2125 2-fluorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2126 3-fluorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2127 4-fluorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2128 2-chlorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2129 4-chlorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2130 2-bromophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2131 2-iodophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2132 3-cyanophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2133 4-cyanophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2134 2-nitrophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2135 3-nitrophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2136 4-nitrophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2137 2-trifluoromethyl phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2138 4-trifluoromethyl phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2139 4-trifluoromethoxy phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2140 2,3-difluorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 4-8] Compound Nos. Q1 R1 A1 A2 Q2 2141 2,4-difluorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2142 2,5-difluorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2143 2,6-difluorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2144 2,4-dichlorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2145 2,6-dichlorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2146 3,4-dichlorophenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2147 2-chloro-4-nitro phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2148 2-chloro-4-fluoro phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2149 2-chloro-6-fluoro phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2150 4-chloro-2-fluoro phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2151 4-chloro-2-nitro phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2152 2,3,6-trifluoro phenyl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2153 pyridine-2-yl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2154 pyridine-3-yl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2155 2-fluoropyridine-3-yl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2156 2-chloropyridine-3-yl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2157 2-chloropyridine-5-yl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2158 2-methylthio pyridine-3-yl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2159 pyrazine-2-yl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2160 furan-2-yl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 4-9] Compound Nos. Q1 R1 A1 A2 Q2 2161 thiophene-2-yl Me N C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2162 phenyl H C N 2,6-dimethyl-4-heptafluoro isopropylphenyl 2163 phenyl H C N-oxide 2,6-dimethyl-4-heptafluoro isopropylphenyl 2164 phenyl H N-oxide C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2165 2-fluorophenyl H N-oxide C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2166 phenyl H N-oxide C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2167 2-fluorophenyl H N-oxide C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2168 phenyl Me N-oxide C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2169 2-fluorophenyl Me N-oxide C 2,6-dimethyl-4-heptafluoro isopropylphenyl 2170 phenyl Me N-oxide C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2171 2-fluorophenyl Me N-oxide C 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl -
[Table 5-1] Compound Nos. G1 G2 Q2 2201 O S 2,6-dimethyl-4-heptafluoroisopropylphenyl 2202 S O 2,6-dimethyl-4-heptafluoroisopropylphenyl 2203 S S 2,6-dimethyl-4-heptafluoroisopropylphenyl 2204 O S 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2205 S O 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2206 S S 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 2207 O S 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 2208 S O 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 2209 S S 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 2210 O S 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl) phenyl 2211 S O 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl) phenyl 2212 S S 2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl) phenyl 2213 O S 2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl 2214 S O 2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl 2215 S S 2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl 2216 O S 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 2217 S O 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 2218 S S 2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl 2219 O S 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 2220 s O 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl -
[Table 5-2] Compound Nos. G1 G2 Q2 2221 S S 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl - The physical properties of the compound represented by the general formula (1) of the present invention are shown in Table 6 below. Tetramethylsilane is used as an internal standard substance to record shift values of 1H-NMR as shown herein, unless otherwise particularly mentioned.
-
[Table 6-1] Compound No. 1H-NMR (DMSO-d6, ppm) 1 (CDCl3) δ 2.36(6H, s), 7.36(2H, s), 7.51-7.65(5H, m), 7.73(1H, d, J = 7.8Hz), 7.86(1H, d, J = 7.8Hz), 7.89(2H, d, J = 7.8Hz), 8.01(1H, s), 8.33(1H, s). 2 δ 7.52-7.63(4H, m), 7.77(1H, d, J = 7.8Hz), 7.98-8.09(5H, m), 8.39(1H, s), 10.48(1H, s), 10.59(1H, s). 3 δ 7.32-7.39(2H, m), 7.54-7.63(2H, m), 7.67-7.72(1H, m), 7.77(1H, d, J = 7.8Hz), 7.98(1H, d, J = 7.8Hz), 8.03(2H, s), 8.34(1H, s), 10.61(1H, s), 10.65(1H, s). 4 δ 7.53-7.63(4H, m), 7.79(1H, d, J = 8.3Hz), 7.99-8.02(2H, m), 8.08(1H, dd, J = 2.0,8.3Hz), 8.17(2H, s), 8.39(1H, d, J = 2.0Hz), 10.50(1H, s), 10.63(1H, s). 5 δ 7.33-7.40(2H, m), 7.54-7.63(2H, m), 7.68-7.72(1H, m), 7.79(1H, d, J = 7.8Hz), 7.99(1H, d, J = 7.8Hz), 8.17(2H, s), 8.35(1H, s), 10.65(1H, s), 10.67(1H, s). 6 δ 7.52-7.62(4H,m), 7.75(1H,d,J=7.8Hz), 7.91(2H,s), 7.97(2H,d,J=7.8Hz), 8.04(1H,d,J=7.8Hz),8.36(1H,s), 10.50(1H,s),10.61(1H,s). 7 δ 7.53-7.64(4H, m), 7.78(1H, d, J = 7.8Hz), 7.99-8.01(2H, m), 8.06(2H, s), 8.09(1H, dd, J = 2.0,7.8Hz). 8.39(1H, s), 10.51(1H, s), 10.63(1H, s). 8 δ 7.33-7.40(2H, m), 7.55-7.63(2H, m), 7.68-7.72(1H, m), 7.78(1H, d, J = 7.8Hz), 7.99(1H, d, J = 7.8Hz), 8.05(2H, s), 8.34(1H, s), 10.65(1H, s), 10.69(1H, s). 9 δ 2.29(6H, s), 7.47(2H, s), 7.51-7.62(4H, m), 7.75(1H, d, J = 7.8Hz), 7.97-8.00(2H, m), 8.03-8.06(1H, m), 8.36(1H, s), 10.00(1H, s), 10.45(1H, s). ' 10 δ 2.37 (6H, s), 7.34 (2H, s), 7.46-7.57 (4H, m), 7.75 (1H, d, J =7.8Hz), 7.98-8.01 (2H, m), 8.12 (1H, d, J =7.3Hz), 8.34 (1H. s). 8.87 (1H, s), 9.66 (1H, s). (CDCl3) δ 2.35 (6H, s), 2.52 (3H, s), 7.26-7.31 (2H, m), 7.36 (2H, s), 7.37-7.42 (1H, m). 7.49-7.54 (2H, m), 7.68-7.73 (3H, m), 7.79 (1H, d, J =7.3Hz), 8.30 (1H, s). 11 12 δ 2.30 (6H, s), 2.41 (3H, s), 7.42-7.48 (4H, m), 7.54 (1H, d, J =7.94Hz), 7.74-7.82 (3H, m), 8.07 (1H, d, J =7.94Hz), 8.35 (1H, s), 9.99 (1H, s), 10.43 (1H, s). 13 δ 2.30 (6H, s), 2.40 (3H, s), 7.35 (2H, d, J =8.3Hz), 7.45 (2H, s), 7.53 (1H, t, J =7.8Hz), 7.74 (1H, d, J =7.81Hz), 7.92 (2H, d, J =8.3Hz), 8.07 (1H, d, J =7.8Hz), 8.36 (1H, s), 9.98 (1H, s), 10.39 (1H, s). 14 δ 1.18 (3H, t J =7.6Hz), 2.30 (6H, s), 2.76 (2H, q, J =7.6Hz), 7.30-7.37 (2H, m), 7.42-7.46 (4H, m), 7.52 (1H, t, J =8.0Hz), 7.81 (1H, d, J =8.0Hz), 7.96 (1H, d, J =8.0Hz), 8.35 (1H, s), 9.98 (1H, s), 10.56(1H, s). 16 δ 1.22 (3H, t, J =7.6Hz), 2.31 (6H, s), 2.69 (2H, q, J =7.6Hz), 7.39 (2H, d, J =8.3Hz), 7.45 (2H, t, J =7.9Hz), 7.53 (2H, d, J=8.3Hz), 7.74 (1H, d, J =7.9Hz), 7.94 (1H, d, J =8.3Hz), 8.07 (1H, d, J =7.9Hz), 8.36 (1H, s), 9.99 (1H, s), 10.40 (1H, s). 17 δ 2.30 (6H, s), 7.33-7.76 (8H, m), 7.97 (1H, d, J =8.30Hz), 8.30 (1H, s), 10.01 (1H, s), 10.65 (1H, s). 18 δ 2.30 (6H, s), 7.45-7.64 (5H, m), 7.76-8.05 (3H, m), 8.06 (1H, d, J =8.3Hz), 8.35 (1H, s), 10.00 (1H, s), 10.54 (1H, s). 19 δ 2.30 (6H, s), 7.37-7.45 (4H, m), 7.54 (1H, t, J =7.8Hz), 7.76 (1H, d, J =7.8Hz), 8.05-8.11 (3H, m), 8.34 (1H, s), 10.00 (1H, s), 10.49 (1H, s). 20 (CDCI3) δ 2.35 (6H, s), 7.36 (2H, s), 7.37-7.54 (4H, m), 7.69-7.83 (4H, m), 8.13 (1H, s), 8.33 (1H, s). 22 δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, dd, J =7.8,6.8Hz), 7.63 (1H, d, J =8.8Hz), 7.72 (1H, d, J =8.8Hz), 7.77 (1H, d, J =6.8Hz), 7.94 (1H, d, J =8.3Hz), 8.03 (1H, d, J =8.8Hz), 8.17 (1H, d, J =7.8Hz). 8.34 (1H, s), 9.99 (1H, s), 10.54 (1H, s). -
[Table 6-2] Compound No. 1H-NMR (DMSO-d6, ppm) 23 (CDCl3) δ 2.36 (6H, s), 7.34-7.38 (3H, m), 7.42-7.46 (1H, m), 7.53 (1H, t, J =7.8Hz), 7.62 (1H, s), 7.65-7.68 (2H, m), 7.73-7.75 (1H, m), 7.82-7.84 (1H, m), 7.89 (1H, s), 8.32 (1H, s). 26 (CDCl3) δ 2.36 (6H, s), 7.19 (1H, dt, J = 2.0,7.8Hz), 7.36 (2H, s), 7.46 (1H, t, J = 7.8Hz), 7.52-7.57 (3H, m), 7.66 (1H, s), 7.74 (1H, d, J = 7.8Hz), 7.85 (1H, d, J = 7.8Hz), 7.94 (1H, d, J = 7.8Hz), 8.31 (1H, s) 28 δ 2.36 (6H, s), 7.33 (2H, s), 7.48 (1H, t, J =7.8Hz), 7.75-7.84 (5H, m), 8.14 (1H, d, J =7.8Hz), 8.31 (1H, s), 9.20 (1H, s), 10.04 (1H, s). 29 δ 2.30 (6H, s), 7.45 (2H, s), 7.57 (1H, d, J =7.8Hz), 7.75-7:80 (2H, m), 8.06-8.11 (2H, m), 8.29 (1H, d, J =7.8Hz), 8.34 (1H, s), 8.46 (1H, s), 10.02 (1H, s), 10.65 (1H, s). 30 δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, t, J =7.8Hz), 7.79 (1 H, d, J =7.8Hz), 8.04-8.06 (3H, m), 8.16 (2H, d, J =8.3Hz), 8.36 (1 H, s), 10.02 (1 H, s), 10.72 (1 H, s). 31 δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, d, J =7.8Hz), 7.76-7.81 (3H, m), 7.88-7.94 (2H, m), 8.1 (1H, d, J =7.8Hz), 8.24 (1 H, s), 10.02 ( 1H, s), 10.90 ( 1H, s). 32 δ 2.32(6H, s), 7.46(2H, s), 7.58(1H, t, J = 7.8Hz), 7.80-7.89(2H, m), 8.11(1H, d, J = 7.8Hz), 8.36(1H, s), 8.44-8.48(2H, m), 8.86(1H, s), 10.04(1H, s), 10.83(1H, s). 33 δ 2.31 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J =8.1Hz), 7.80 (1H, d, J =8.1Hz), 8.08 (1H, d, J =8.1Hz), 8.24 (1H, s), 8.36-8.41 (4H, m), 10.01 (1H, s), 10.79 (1H, s). 34 δ 2.30 (6H, s), 6.39 (2H, s), 6.58-6.62 (1H, m), 6.76 (1H, dd, J =1.0,8.3Hz), 7.19-7.24 (1H, m), 7.45 (2H, s), 7.51 (1H, t, J =7.8Hz), 7.66-7.73 (2H, m), 7.94-7.97 (1H, m), 8.30 (1 H, d, J =2.0Hz), 9.96 (1H, s), 10.20 (1H, s). 35 δ 2.30 (6H, s), 6.53-6.86 (1H, m), 7.20-7.21 (4H, m), 7.45 (2H, s), 7.52 (1 H, t, J =7.8Hz), 7.73 (1H, d, J =7.8Hz), 8.02 (1H, d, J =7.8Hz), 8.35 (1H, s), 9.96 (1H, s), 10.32 (1H, s). 37 (CDCl3) δ 2.34 (6H, s), 7.35 (2H, s), 7.51 (1H, t, J =7.8Hz), 7.62-7.80 (8H, m), 8.25 (1H, s). 39 δ 2.31(6H, s), 7.45(2H, s), 7.57(1H, t, J = 7.8Hz), 7.79(1H, d, J = 7.8Hz), 7.94(2H, d, J = 8.3Hz), 8.07(1H, d, J = 7.8Hz), 8.20(2H, d, J = 8.3Hz), 8.36(1H, s), 10.01(1H, s), 10.70(1H, s). 40 δ 2.30 (6H, s), 6.96-7.01 (2H, m), 7.43-7.48 (3H, m), 7.56 (1H, t, J =8.3Hz), 7.78 (1H, d, J =8.3Hz), 7.97-8.00 (2H, m), 8.29 (1H, s), 10.01 (1H, s), 10.61 (1H, s). 41 δ 2.30(6H, s), 3.90(3H, s), 7.05-7.10(1H, m), 7.19(1H, d, J = 8.3Hz), 7.45(2H, s), 7.49-7.54(2H, m), 7.63(1H, dd, J = 2.0,7.8Hz), 7.72(1H, d, J = 7.8Hz), 7.96(1H, d, J = 7.8Hz), 8.33(1H, s), 9.98(1H, s), 10.33(1H, s). 45 δ 1.33 (9H, s), 2.31 (6H, s), 7.45 (2H, s), 7.53 (1H, t, J =7.8Hz), 7.54 (2H,d,J = 8.3Hz), 7.74 (1H, d, J =7.8Hz), 7.94 (2H, d, J =8.3Hz), 8.06 (1 H, d, J =7.8Hz), 8.36 (1H,s), 9.99 (1H, s), 10.40 (1H, s). 46 δ 2.30 (6H, s), 2.98 (6H, s), 6.93-6.95 (1H, m), 7.25-7.35 (3H, m), 7.45 (2H, s), 7.53 (1H, t, J =7.8Hz), 7.74 (1H, d, J =7.8Hz), 8.06 (1H, d, J =7.8Hz), 8.35 (1H, s), 9.99 (1H, s), 10.35 (1H, s). 47 δ 2.30 (6H, s), 3.01 (6H, s), 6.77 (2H, d, J =9.3Hz), 7.45 (2H, s), 7.50 (1H, t, J =7.8Hz), 7.69 (1H, d, J =7.8Hz), 7.91 (2H, d, J =9.3Hz), 8.06 (1H, d, J =7.8Hz), 8.33 (1H, s), 9.96 (1H, s), 10.09 (1H, s). 48 δ 2.31(6H, s), 7.45(2H, s), 7.53-7.60(3H, m), 7.77(1H, d, J = 7.3Hz), 8.06(1H, d, J = 8.3Hz), 8.13(2H, d, J = 8.3Hz), 8.35(1H, s), 10.01(1H, s), 10.59(1H, s). 52 8 2.21 (3H, s), 2.30 (6H, s), 7.27 (1H, d, J =8.3Hz), 7.39-7.44 (1H, m), 7.45 (2H, s), 7.50-7.62 (2H, m), 7.70-7.52 (2H, m), 7.92 (1H, d, J =7.8Hz), 8.29 (1H, s), 9.99 (1 H, s), 10.57 (1H, s). 54 δ 2.30 (6H, s), 3.91 (3H, s), 7.45 (2H, s), 7.56 (1H, t, J =7.8Hz), 7.78 (1H, d, J =7.8Hz), 8.03-8.15 (5H, m), 8.36 (1H, s), 10.01 (1H, s), 10.67 (1H, s). -
[Table 6-3] Compound No. 1H-NMR (DMSO-d6, ppm) 56 δ 2.27 (6H, s), 2.30 (6H, s), 7.18-7.22 (1 H, m), 7.26-7.30 (2H, m), 7.45 (2H, s), 7.52 (1H, t, J =7.8Hz), 7.72 (1H, d, J =7.8Hz), 7.95 (1H, d, J =7.8Hz), 8.36 (1H, s), 9.98 (1H, s), 10.52 (1H, s). 57 δ 2.30 (6H, s), 2.33 (3H, s), 2.38 (3H, s), 7.11-7.13 (2H, m), 7.40 (1H, d, J =7.8Hz), 7.44 (2H, s), 7.51 (1H, t, J =7.8Hz), 7.72 (1H, d, J =7.8Hz), 7.95 (1H, d, J =8.8Hz), 8.34 (1H, s), 9.98 (1H, s), 10.43 (1H, s). 58 δ 2.30 (12H, s), 7.12 (2H, d, J =7.8Hz), 7.23-7.27 (1H, m), 7.45 (2H, s), 7.52 (1H, t, J =8.3Hz), 7.75 (1H, d, J =8.3Hz), 7.94-7.99 (1H, m), 8.35 (1H, s), 10.00 (1H, s), 10.61 (1H, s). 59 δ 2.30 (6H, s), 7.34-7.40 (1H, m), 7.45 (2H, s), 7.50-7.58 (2H, m), 7.60-7.68 (1H, m), 7.77 (1 H, d, J =7.8Hz), 7.96 (1H, d, J =8.3Hz), 8.31 (1H, s), 10.02 (1H, s), 10.78 (1H, s). 60 δ 2.30 (6H, s), 7.22-7.28 (1H, m), 7.42-7.48 (3H, m), 7.53-7.57 (1H, m), 7.75-7.82 (2H, m), 7.96 (1 H, d, J =7.8Hz). 8.30 (1H, s), 10.01 (1H, s), 10.65 (1H, s). 61 δ 2.30 (6H, s), 7.45 (2H, s), 7.46-7.49 (2H, m), 7.53-7.59 (2H, m), 7.77 (1H, d, J =7.8Hz), 7.96 (1H, d, J =8.3Hz), 8.30 (1H, s), 10.02 (1H, broad), 10.72 (1H, broad). 62 δ 2.30 (6H, s), 7.25-7.30 (2H, m), 7.45 (2H, s), 7.54-7.65 (2H, m), 7.77 (1H, d, J =7.8Hz), 7.93 (1H, d, J =7.8Hz), 8.29 (1H. s), 10.03 (1H, s), 11.04 (1H, s). 66 δ 2.30(6H, s), 7.45(2H, s), 7.52-7.62(2H, m), 7.66(1H, d, J = 8.3Hz), 7.75-7.80 (2H, m), 7.94(1H, d, J = 7.8Hz), 8.30(1H, s), 10.02(1H, s), 10.77(1H, s). 68 δ 2.30 (6H, s), 7.45 (2H, s), 7.50-7.62 (4H, m), 7.78 (1H, d, J =7.8Hz), 7.94 (1H, d, J =7.8H z), 8.28 (1H, s), 10.03 (1H, s), 10.99 (1H. s). 69 δ 230(6H, s), 7.45(2H, s), 7.56(1H, t, J = 7.8Hz), 7.79(1H, d, J = 7.8Hz), 7.85(1H, d, J =8.3Hz), 7.97-8.00(1H, m), 8.05-8.08(1H, m), 8.27(1H, d, J = 2.0Hz), 8.33(1H, s), 10.00(1H, s), 10.61(1H, s). 70 δ 274(6H, s), 7.34(2H, s), 7.52(1H, t, J = 7.8Hz), 7.81(1H, d, J = 7.8Hz), 7.93(1H, d, J = 8.3Hz), 8.13-8.15(2H, m), 8.58(1H, d, J = 8.3Hz), 8.94(1H, s), 9.27(1H, s), 10.67(1H, s). 71 (CDCl3) δ 1.6-2.4(6H, broad-s), 6.5-7.7(3H, broad), 7.8-8.0(4H, broad), 8.10(1H, broad-s), 8.28(1H, d, J = 8.8Hz). 72 δ 2.30 (6H, s), 3.78 (6H, s), 6.66-6.75 (2H, m), 7.34-7.50 (4H, m), 7.67 (1H, d, J =7.8Hz), 7.91 (1H, d, J =7.8Hz), 8.34 (1H, s), 9.98 (1H, s), 10.44 (1H, s). 73 δ 2.30 (6H, s), 3.83 (6H, s), 6.73 (1H, t, J =2.4Hz), 7.15 (2H, d, J =2.4Hz), 7.45 (2H, s), 7.54 (1H, t, J =8.3Hz), 7.75 (1H, d, J =8.3Hz), 8.06 (1H, d, J =8.3Hz), 8.33 (1H, s), 9.99 (1H, s), 10.39 (1H, s). 74 (CDCl3) δ 234(6H, s), 2.68(3H, s), 7.36(2H, s), 7.55(1H, t, J = 7.8Hz), 7.62(1H, s), 7.72(1H, d, J = 7.8Hz), 7.81(1H, d, J = 8.3Hz), 7.88(1H, s), 7.92(1H, d, J = 7.8Hz), 8.05(1H, d, J = 8.3Hz), 8.17(1H, s), 8.26(1H, s). 75 δ 2.30 (6H, s), 5.22 (2H, broad-s), 6.67-6.72 (1H, m), 6.78-6.81 (1H, m), 6.97-7.02 (1H, m), 7.45 (2H, s), 7.52 (1H, t, J =7.8Hz), 7.72 (1H, d, J =7.8Hz), 7.94 (1H, d, J =7.8Hz), 8.32 (1H, s), 9.98 (1H, s), 10.46 (1H, s). 77 δ 2.30 (6H, s), 7.45 (2H, s), 7.58 (1H, t, J =7.8Hz), 7.70 (1H, t, J=8.8Hz), 7.80 (1H, d, J =7.8Hz), 7.99 (1H, d, J =7.8Hz), 8.29 (1H, s), 8.45-8.50 (1H, m), 8.57-8.60 (1H, m), 10.03 (1H, s), 10.91 (1H, s). 81 δ2.30 (6H, s), 7.56 (1H, t), 7.73-7.80 (6H, m), 7.92 (1H, d, J =7.81 Hz), 8.22 (1H, s), 10.03 (1H, s), 11.05 (1H,s). 82 δ2.30 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J =7.8Hz), 7.80 (1H, d, J =7.8Hz), 7.92-7.96 (2H, m), 8.29-8.45 (2H, m), 8.45 (1H, m), 10.03 (1H, s), 10.98 (1H, s). 83 δ2.28 (6H, s), 7.33-7.38 (1H, m), 7.43 (2H, s), 7.53 (1H, t, J=7.9Hz), 7.58 (1H, d, J =2.4Hz), 7.61-7.71 (1H, m), 7.75 (1H, d, J =7.9Hz), 7.93 (1H, d, J =7.9Hz), 8.28 (1H, s), 9.98 (1H, s), 10.71 (1H, s). -
[Table 6-4] Compound No 1H-NMR (DMSO-d6, ppm) 84 δ 2.30 (6H, s), 7.38-7.48 (4H, m), 7.54-7.60 (2H, m), 7.78 (1H, d, J =7.8Hz), 7.93 (1H, d, J =7.8Hz), 8.28 (1H, s), 10.03 (1H, s), 11.03 (1H, s). 86 δ 2.30 (6H, s), 7.42-7.47 (3H, m), 7.55 (1H, t, J =8.0Hz), 7.64 (1H, d, J =2.0Hz), 7.66-7.77 (2H, m), 7.96 (1H, d, J =8.0Hz), 8.29 (1H, s), 10.01 (1H, s), 10.69 (1H, s). 87 δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, t, J =7.9Hz), 7.79 (1H, d, J =7.9Hz), 7.87 (1H, d, J =7.9Hz), 7.92 (1H, dd, J =8.2,1.6Hz), 8.00 (1H, dd, J =8.2,1.6Hz), 8.22 (1H, t, J =1.6Hz), 8.29(1H, d,J = 1.6Hz), 10.03 (1H, s), 10.94 (1H, s). 88 (CDCl3) δ 237(6H, s), 4.06(3H, s), 7.37(2H, s), 7.44(1H, d, J = 9.7Hz), 7.52(1H, s), 7.58(1H, t, J = 7.8Hz), 7.70(1H, s), 7.74(1H, d. J = 7.8Hz). 7.93(1H, s), 7.95(1H, s), 8.02(1H, s), 8.26(1H, s). 89 (CDCl3) δ 237(6H, s), 4.22(3H, s), 7.37(2H, s), 7.55(1H, t, J = 7.8Hz), 7.56(1H, s), 7.72(1H, d, J = 7.8Hz), 7.94-7.97(2H, m), 8.00(1H, d, J = 7.8Hz), 8.28(1H, s), 8.47(1H, d, J = 8.8Hz), 9.83(1H, s). 91 δ 2.25 (6H, s), 2.27 (3H, s), 2.29 (6H, s), 6.94 (2H, s), 7.45 (2H, s), 7.51 (1H, t, J =7.8Hz), 7.73 (1H, d, J =7.8Hz), 7.94 (1H, d, J =7.8Hz), 8.34 (1H, s), 9.97 (1H, s), 10.53 (1H, s). 92 δ 2.33 (6H, s), 7.32-7.40 (1H, m), 7.45 (2H, s), 7.58 (1H, t, J =8.06Hz), 7.67-7.75 (1H, m), 7.80 (1H, d, J =7.81Hz), 7.92 (1H, d, J =8.29Hz), 8.27 (1H, s), 10.04 (1H, s), 11.14 (1H, s). 95 δ 2.30 (6H, s), 7.45 (2H, s), 7.59 (1H, t, J =7.8Hz), 7.83 (1H, d, J =7.8Hz), 7.91-7.94 (1H, dd, J =1.5,7.8Hz), 8.25 (1H, d, J = 1.5Hz), 10.06 (1H, s), 11.27 (1H, s). 96 δ 2.30 (6H, s), 7.28-7.55 (10H, m), 7.57-7.61 (2H, m), 7.69 (1H, d, J =7.8Hz), 7.74 (1H, d, J =7.8Hz), 8.13 (1H, s), 9.94 (1H, s), 10.47 (1H, s). 97 δ 2.32 (6H, s), 7.41-7.57 (6H, m), 7.72-7.82 (3H, m), 7.85-7.88 (2H, m), 8.09-8.13 (3H, m), 8.40 (1H, s), 10.01 (1H, s), 10.53 (1H, s). 98 δ 231(6H, s), 7.45(2H, s), 7.54-7.65(4H, m), 7.76-7.80(2H, m), 8.01-8.06(2H, m), 8.10(1H, d, J = 8.3Hz), 8.21-8.23(1H, m), 8.43(1H, s), 10.01(1H, s), 10.80(1H, s). 99 δ 2.32(6H, s), 7.46(2H, s), 7.57(1H, t, J = 7.8Hz), 7.61-7.72(2H, m), 7.78(1H, d, J = 7.8Hz), 7.99-8.17(5H, m), 8.41(1H, t, J = 2.0Hz), 8.65(1H, s), 10.01(1H, s), 10.66(1H, s). 100 δ2.31 (6H, s), 7.45 (2H, s), 7.55 (1H, t, J =7.8Hz), 7.69-7.76 (2H, m), 8.07-8.14 (2H, m), 8.19 (1H, d, J =7.8Hz), 8.54 (1H, s), 8.77 (1H, d, J =4.9Hz), 9.99 (1H, s), 10.86 (1H, s). 101 δ 2.30 (6H, s), 7.45 (2H, s), 7.54-7.61 (2H, m), 7.78 (1H, d, J =8.3Hz), 8.06 (1H, d, J =7.3Hz), 8.32-8.35 (2H, m), 8.77-8.79 (1H, m), 9.14 (1H, d, J =1.5Hz), 10.00 (1H, s), 10.66 (1H, s). 102 δ 2.30 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J =7.8Hz), 7.80 (1H, d, J =7.8Hz), 7.91 (2H, d, J =5.6Hz), 8.06 (1H, d, J =7.8Hz), 8.35 (1H, s), 8.81 (2H, d, J =5.6Hz), 10.01 (1H, s), 10.72 (1H, s). 103 δ 2.27 (3H, s), 2.30 (6H, s), 7.45 (2H, s), 7.54-8.07 (6H, m), 8.35 (1H, s), 10.02 (1H, s), 10.77 (1H, s). 105 δ 2.30 (6H, s), 7.45 (2H, s), 7.52-7.58 (2H, m), 7.78 (1H, d, J =8.30Hz), 7.97 (1H, d, J =8.29Hz), 8.26-8.31 (2H, m), 8.42 (1H, d, J =4.39Hz), 10.02 (1H, s), 10.80 (1H, s). 106 δ 2.30 (6H, s), 7.45 (2H, s), 7.54-7.60 (2H, m), 7.77-7.81 (1H, m), 7.95 (1H, d, J =7.8Hz), 8.10-8.13 (1H, m), 8.30 (1H, s), 8.54-8.59 (1H, m), 10.03 (1H, s), 10.88 (1H, s). 108 δ 2.31 (6H, s), 7.45 (2H, s), 7.56 (1 H, t, J =7.8Hz), 7.78 (1H, d, J =7.8Hz), 7.82 (1H, dd, J =6.3,2.4Hz), 8.11-8.16 (3H, m), 8.47 (1H, s), 10.01 (1H, s), 10.69 (1H, s). 109 δ 2.31 (6H, s), 7.46 (2H, s), 7.57 (1H, t, J =8.3Hz), 7.74 (1H, d, J =8.3Hz), 7.80 (1H, d, J =8.3Hz), 8.06 (1H, dd, J =8.3,1.7Hz), 8.34 (1H, t, J =1.7Hz), 8.40(1H, dd, J = 8.3,1.7Hz), 9.00 (1H, d, J =1.7Hz), 10.02 (1H, s), 10.71 (1H, s). -
[Table 6-5] Compound No. 1H-NMR (DMSO-d6, ppm) 110 δ 2.31 (6H, s), 7.45 (2H, s), 7.56 (1H, d, J =8.1Hz), 7.78 (1H, d, J =8.1Hz), 7.86 (1H, d, J =2.1Hz), 8.11 (1H, dd, J =8.1,2.1Hz), 8.19 (1H, d, J =2.1Hz), 8.53 (1H, t, J =2.1Hz), 8.75 (1H, d, J =5.4Hz), 10.01 (1H, s), 10.96 (1H, s). 111 (CDCl3) δ 2.36 (6H, s,), 7.34 (2H, s,), 7.47-8.94 (7H, m,), 9.63 (1H, s,), 10.73 (1H, s,). 113 (CDCl3) δ 2.36 (6H, s,), 7.34-8.73 (15H, m,), 10.01 (1H, s,) 114 δ 2.30 (6H, s), 2.42 (3H, s), 7.25-7.28(1H, m), 7.44 (2H, s), 7.55 (1H, t, J =7.8Hz), 7.77 (1H, d, J =7.8Hz), 7.94-7.97(2H, m), 8.30 (1H, s), 8.61 (1H, dd, J =4.9,1.5Hz), 10.00 (1H, s), 10.67 (1H, s). 115 δ 2.29 (6H, s), 3.94 (3H, s), 4.06 (3H, s), 6.53 (1H, d, J =8.3Hz), 7.44 (2H, s), 7.51 (1H, t, J =7.9Hz), 7.72 (1H, d, J =7.9Hz), 7.95 (1H, d, J =7.9Hz), 8.12 (1H, d, J =8.3Hz), 8.28 (1H, s), 9.96 (1H, s), 10.07 (1H, s). 116 δ2.29 (6H, s), 7.44 (2H, s), 7.57 (1H, t, J =7.9Hz), 7.80 (1H, d, J =7.9Hz), 8.05 (1H, d, J =7.9Hz), 8.30 (1H, s), 8.67 (1H, d, J =2.2Hz), 8.93 (1H, d, J =2.2Hz), 10.01 (1H, s), 10.73 (1H, s). 117 (CDCl3) δ 2.36 (6H, s), 7.37-8.50 (9H, m,), 8.97 (1H, s). 118 δ2.28 (6H, s), 7.43 (2H, s), 7.56 (1H, t, J =8.0Hz), 7.74-7.79 (2H, m), 7.92 (1H, d, J =8.0Hz), 8.20 (1H, d, J =8.3Hz), 8.25 (1H, s), 10.01 (1H, s), 10.88 (1H, s). 119 (CDCl3) δ 2.36 (6H, s), 7.36-8.60 (10H, m,). 120 δ 2.31 (6H, s), 7.46 (2H, s), 7.57 (1H, t, J =7.8Hz), 7.80 (1H, d, J =7.8Hz), 8.02 (1H, d, J =7.8Hz), 8.08 (2H, d, J =1.2Hz), 8.33 (1H, t, J =20Hz), 8.40 (2H, d, J =7.3Hz), 10.02 (1H, s), 10.63 (1H, s). 121 δ 2.30 (6H, s), 3.89 (3H, s), 6.11 (1H, dd, J =2.0,3.9Hz), 7.03 (1H, t, J =2.0Hz), 7.10 (1H, dd, J =2.0,3.9Hz), 7.45 (2H, s), 7.49 (1H, t, J =7.8Hz), 7.69 (1H, d, J =7.8Hz), 7.99 (1H, d, J =7.8Hz), 8.28 (1H, s), 9.95 (2H, s). 122 δ2.31 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J =7.8Hz), 7.78 (1H, d, J =7.8Hz), 8.11 (1H, d, J =7.8Hz), 8.53 (1H, s), 8.84 (1H, dd, J =1.5,2.4Hz), 8.95 (1H, d, J =24Hz), 9.33 (1H, d, J =1.5Hz), 10.00 (1H, s), 10.97 (1H, s). 124 δ 2.28 (6H, s), 7.44 (2H, s), 7.58 (1H, t, J =7.9Hz), 7.81 (1H, d, J =7.9Hz), 7.92 (1H, d, J =7.9Hz), 8.20 (1H, s), 9.43 (1H, s), 9.59 (1H, s), 10.03 (1H, s), 11.06 (1H, s). 125 δ2.30 (6H, s), 7.45 (2H, s), 7.50-7.62 (4H, m), 7.78 (1H, d, J =7.8Hz), 7.94 (1H, d, J =7.8Hz), 8.28 (1H, s), 10.03 (1H, s), 10.99 (1H, s). 126 δ2.30 (6H, s), 7.04 (1H, t, J =1.5Hz), 7.45 (2H, s), 7.53 (1H, t, J =8.0Hz), 7.74-7.82 (2H, m), 8.04 (1H, d, J =1.5Hz), 8.25 (1H, d, J =1.5Hz), 8.43 (1H, t, J =1.5Hz), 9.98 (1H, s), 10.14 (1H, s). 127 δ 1.86-1.91 (2H, m), 200-2.02 (1H, m), 2.19-2.29 (7H, m), 3.81-3.87 (1H, m), 3.98-4.03 (1H, m), 4.40-4.43 (1H, m), 7.44-7.50 (3H, m), 7.77 (1H, d, J =7.8Hz), 7.94 (1H, d, J =7.8Hz), 8.26 (1H, s), 9.89 (1H, s), 9.94 (1H, s). 128 (CDCl3) δ 202-2.10 (2H, m), 2.28 (6H, s), 3.15-3.22 (1H, m), 3.80-3.98 (4H, m), 7.44 (2H, s), 7.48 (1H, t, J=7.8 Hz), 7.68 (1H, t, J=7.8 Hz), 7.87 (1H, d, J=7.8 Hz), 8.16 (1H, s), 9.96 (1H, s), 10.3 (1H, s). 129 (CDCl3) δ 222(6H, s), 7.17-7.28(3H, m), 7.33-7.39(2H, m), 7.42-7.48(2H, m), 7.58-7.65(2H, m), 7.79(1H, dd, J = 1.5,8.3Hz), 7.91(1H, s), 8.27(1H, s), 8.51(1H, s). 130 (CDCl3) δ 1.48-2.17(6H, m), 2.34(6H, s), 3.52-3.60(1H, m), 3.92(1H, dd, J = 2.5,11.2Hz), 4.11-4.18(1H, m), 7.35(2H, s), 7.47(1H, t, J = 7.8Hz), 7.60(1H, broad), 7.69(1H, d, J = 7.8Hz), 7.77(1H, dd, J = 1.0,7.8Hz), 8.26(1H, s), 8.54(1H, s). 131 δ 1.97-2.07 (2H, m), 2.15-2.31 (9H, m), 2.97-3.07 (2H, m), 3.99-3.98 (2H, m), 7.46 (2H, s), 7.55 (1H, t, J =8.0Hz), 7.65 (1H, d, J =8.0Hz), 7.87 (1H, d, J =8.0Hz), 8.20 (1H, s), 9.60 (1H, s), 9.91 (1H, s). -
[Table 6-6] Compound No. 1H-NMR (DMSO-d6, ppm) 132 (CDCl3) δ 2.35(6H, s), 7.16(1H, dd, J = 3.9,4.9Hz), 7.36(2H, s), 7.51(1H, t, J = 7.8Hz), 7.59 (1H, dd, J = 1.0,4.9Hz), 7.67(1H, dd, J = 1.0,3.9Hz), 7.70-7.74(2H, m), 7.80-7.83(1H, m), 7.95 (1H, s), 8.27(1H, s). 133 δ 2.30 (6H, s), 7.45 (2H, s), 7.54 (1H, t, J =8.0Hz), 7.67 (2H, d, J =2.4Hz), 7:75 (1H, d, J =7.8Hz), 8.07 (1H, d, J =7.8Hz), 8.31 (1H, s), 8.41 (1H, t, J =2.2Hz), 9.99 (1H, s), 10.28 (1H, s). 134 δ 2.30 (6H, s), 2.47 (3H, s), 7.04 (1H, d, J =4.2Hz), 7.45 (2H, s), 7.52 (1H, t, J =7.8Hz), 7.69 (1H, d, J =4.2Hz), 7.74 (1H, d, J =7.8Hz), 7.93 (1H, d, J =7.8Hz), 8.27 (1H, s), 9.97 (1H, s), 10.17 (1H, s). 135 δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, t, J =7.8Hz), 7.79 (1H, d, J =7.8Hz), 8.08 (1H, d, J =7.8Hz), 8.30 (1H, s), 8.71 (1H, d, J =2.0Hz), 8.74 (1H, d, J =2.0Hz), 10.01 (1H, s), 10.54 (1H, s). 136 δ 2.30 (6H, s), 2.50 (3H, s), 6.94 (1H, d, J =3.4Hz), 7.45 (2H, s), 7.52 (1H, t, J =7.9Hz), 7.74 (1H, d, J =7.9Hz), 7.88 (1H, d, J =3.4Hz), 8.02 (1H, d, J =7.9Hz), 8.27 (1H, s), 9.97 (1H, s), 10.32 (1H, s). 137 δ 2.29 (6H, s), 7.22 (1H, d, J =5.1Hz), 7.43 (2H, s), 7.53 (1H, t, J =8.0Hz), 7.76 (1H, d, J =8.0Hz), 7.91-7.93 (2H, m), 8.26 (1H, s), 9.98 (1H, s), 10.42 (1H, s). 138 δ 2.30 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J =8.1Hz), 7.79 (1H, d, J =8.1Hz), 8.05 (1H, d, J =8.1Hz), 8.52 (1H, s), 9.97 (1H, s), 11.11 (1H, s). 139 δ 2.30 (6H, s), 7.26 (1H, d, J =5.4Hz), 7.45 (2H, s), 7.54 (1H, t, J =8.0Hz), 7.77 (1H, d, J =8.0Hz), 7.90-7.94 (2H, m), 8.27 (1H, s), 9.99 (1H, s), 10.50 (1H, s). 140 δ 2.30 (6H, s), 7.39 (1H, d, J =4.6Hz), 7.45 (2H, s), 7.54 (1H, t, J =8.1 Hz), 7.77 (1H, d, J =8.1Hz), 7.92 (1H, d, J =4.6Hz), 8.02 (1H, d, J =8.1Hz), 8.26 (1H, s), 9.99 (1H, s), 10.50 (1H, s). 141 δ 2.30 (6H, s), 7.29 (1H, d, J =4.9Hz), 7.45 (2H, s), 7.55 (1H, t, J =7.9Hz), 7.77 (1H, d, J =7.9Hz), 7.81 (1H, d, J =4.9Hz), 7.92 (1H, d, J =7.9Hz), 8.29 (1H, s), 10.00 (1H, s). 10.50 (1H, s). 142 δ 2.27 (6H, s), 7.25-7.52 (10H, m), 7.70-7.73 (1H, m), 7.81-7.20 (1H, m), 8.12 (1H, s), 9.94 (1H, s), 10.27 (1H, s). 143 δ 2.28 (6H, s), 2.40 (3H, s), 2.45 (3H, s), 6.74 (1H, s), 7.43 (2H, s), 7.49 (1H, t, J =8.1Hz), 7.71 (1H, d. J =8.1Hz), 7.90 (1H, d, J =8.1Hz), 8.24 (1H, s), 9.94 (1H, s), 9.98 (1H, s). 144 δ 231(6H, s), 7.41-7.59(5H, m), 7.78(1H, d, J = 7.8Hz), 8.00-8.09(3H, m), 8.34(1H, d, J = 2.0Hz), 8.43(1H, s), 10.02(1H, s), 10.75(1H, s). 146 δ 0.86 (3H, 7.2), 2.30 (6H, s), 4.34 (2H, q, J =7.2Hz), 7.45 (2H, s), 7.77-7.79 (3H, m), 7.84 (1H, s), 8.24 (1H, s), 8.37 (1H, s), 10.05 (1H, s), 11.11 (1H, s). 147 δ 2.30 (6H, s), 3.89 (3H, s), 7.45 (2H, s), 7.52 (1H, t, J =7.9Hz), 7.73 (1H, d, J =7.9Hz), 7.97 (1H, d, J =7.9Hz), 8.23 (1H, s), 8.45 (1H, s), 9.98 (1H, s), 10.08 (1H, s). 148 δ 2.35 (6H, s), 3.92 (3H, s), 7.26 (1H, s), 7.36 (2H, s), 7.48-7.55(2H, m)" 7.70 (1H, d, J =7.7Hz), 7.83 (1H, d, J =7.7Hz), 8.26 (1H, s), 8.47 (1H, s). 149 δ 2.36 (6H, s), 3.95 (3H, s), 7.26 (1H, s), 7.36 (2H, s), 7.50 (1H, t, J =7.7Hz), 7.70 (1H, d, J =7.7Hz), 7.83 (1H, d, J =7.7Hz), 8.00 (1H, s), 8.26 (1H, s), 8.58 (1H, s). 150 (CDCl3) δ 235(6H, s), 4.01(3H, s), 7.36(2H, s), 7.51(1H, t, J = 7.8Hz), 7.68-7.73 (3H, m), 7.92(1H, s), 8.05(1H, s), 8.25(1H, s). 151 δ 2.29 (6H, s), 4.06 (3H, s), 7.44 (2H, s), 7.53 (1H, t, J =7.9Hz), 7.77 (1H, d, J =7.9Hz), 7.96 (1H, d, J =7.9Hz), 8.11 (1H, s), 8.26 (1H, s), 10.02 (1H, s), 10.58 (1H, s). 152 δ 2.30 (6H, s), 7.32 (1H, d, J =20Hz), 7.45 (2H, s), 7.58 (1H, t, J =7.8Hz), 7.81 (1H, d, J =7.8Hz), 8.04 (1H, d, J =7.8Hz), 8.35 (1H, s), 8.84 (1H, d, J =2.0Hz), 10.03 (1H, s), 10.97 (1H, s). -
[Table 6-7] Compound No. 1H-NMR (DMSO-d6, ppm) 153 δ 2.29 (6H, s), 7.46 (2H, s), 7.64 (1H, t), 7.72 (1H, d, J =1.0Hz), 7.81 (1H, s), 7.97 (1H, d, J =8.0Hz), 8.17 (1H, s), 8.34 (1H, s), 10.04 (1H, s). 154 δ 2.29 (6H, s), 2.51 (3H, s), 2.56 (3H, s), 7.46 (2H, s), 7.53 (1 H, t, J =8.03Hz), 7.75 (1H, d, J =8.03Hz), 7.92 (1H, d, J =8.03Hz), 8.24 (1H, s), 9.79 (1H, s), 10.30 (1H, s). 155 δ 1.36 (3H, t, J =7.3Hz), 2.30 (6H, s), 2.73(3H, s), 3.05 (2H, q, J =7.3Hz), 7.45 (2H, s), 7.55 (1H, t, J =8.3Hz), 7.78 (1H, d, J =8.3Hz), 7.98 (1H, d, J =8.3Hz), 8.29 (1H, s), 10.01(1H, s), 10.69 (1H, s). 156 δ 2.28 (6H, s), 2.57 (3H, s), 7.43 (2H, s), 7.53 (1H, t, J =7.8Hz), 7.77 (1H, d, J =7.8Hz), 7.91 (1H, d, J =7.8Hz), 8.21 (1H, s), 9.98 (1H, s), 10.47 (1H, s). 157 δ 2.31 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J =7.8Hz), 7.79 (1H, d, J =7.8Hz), 8.06 (1H, d, J =7.8Hz), 8.53 (1H, s), 10.00 (1H, s), 11.12 (1H, s). 158 δ 2.36 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J =8.1 Hz), 7.79 (1H, d, J =8.1 Hz), 8.06 (1H, d, J =8.1 Hz), 8.53 (1H, s), 10.01 (1H, s), 11.11 (1H, s). 159 δ 2.30(6H, s), 7.45(2H, s), 7.56-7.66(3H, m), 7.80(1H, d, J = 8.3Hz), 7.94-7.98(2H, m), 8.16-8.20(1 H, m), 8.32(1 H, s), 10.04(1 H, s), 10.79(1 H, s). 160 δ 2.31 (6H, s), 7.45(2H, s), 7.53-7.61(2H, m), 7.78(1H, d, J = 7.8Hz), 7.92-7.95(1H, m), 8.02-8.07(2H, m), 8.34(1 H, s), 9.99( 1H, s), 10.50( 1H, s). 161 δ 2.30(6H, s), 7,37(1H, t, J = 7.8Hz), 7.45(2H, s), 7.57(1H, t, J = 7.8Hz), 7.62-7.65(2H, m), 7.79(1H, d, J = 7.8Hz), 7.99(1H, d, J = 7.8Hz), 8.30(1H, s), 10.01(1H, s), 10.65(1H, s). 163 δ 2.38 (3H, s), 7.53-7.63 (4H, m), 7.70 (1H, s), 7.77 (1H, d, J =7.8Hz), 7.81 (1H, s), 7.99-8.01 (2H, m), 8.08 (1H, d, J =7.8Hz), 8.37 (1H, s), 10.28 (1H, s), 10.50 (1H, s). 164 (CDCl3) δ 1.20 (3H, t, J =7.3Hz), 2.32 (3H, s), 2.67 (2H, q, J =7.3Hz), 7.36 (2H, s). 7.46-7.51 (3H, m), 7.55-7.59 (1H, m), 7.67-7.72 (2H, m), 7.85-7.88 (3H, m), 8.15 (1H, s), 8.28 (1H, s). 165 δ 1.13(3H, t, J = 7.3Hz), 2.29(3H, s), 2.67(2H, q, J = 7.3Hz), 7.33-7.41(3H, m), 7.47(1H, s). 7.52-7.63(2H, m), 7.67-7.76(2H, m), 7.97(1H, d, J = 7.8Hz), 8.32(1H, s), 10.01(1H, s), 10.65(1H, s). 166 δ 2.36 (3H, s), 7.53-7.63 (4H, m), 7.68 (1 H, s), 7.79 (1 H, d, J =7.8Hz), 7.96 (1 H, s), 7.99-8.01 (2H, m), 8.08 (1 H, dd, J =1.5,7.8Hz), 8.38 (1 H, d, J =1.5Hz), 10.27 (1 H, s), 10.50 (1H, s). 167 (CDCl3) δ 2.48(3H, s), 7.05(1H, s), 7.23(1H, s), 7.50-7.62(4H, m), 7.69(1H, d, J = 7.8Hz), 7.84(1H, dd, J = 2.0,7.8Hz), 7.89(2H, d, J = 6.8Hz), 8.13(1H, s), 8.16(1H, d, J = 6.8Hz), 8.39(1H, t, J = 1.9Hz), 8.89(1H, s). 168 δ 1.15(3H, t, J = 7.3Hz), 2.73(2H, q, J = 7.3Hz), 7.50-7.63(5H, m), 7.71-7.77(2H, m), 7.94-8.01(2H, m), 8.08(1H, d, J = 7.8Hz), 8.37(1H, s), 10.28(1H, s), 10.50(1H, s). 169 δ 1.14(3H, t, J = 7.3Hz), 2.73(2H, q, J = 7.3Hz), 7.52-7.64(5H, m), 7.76(1H, d, J = 7.8Hz), 7.83(1H, d, J = 2.0Hz), 7.98-8.01(2H, m), 8.06-8.09(1H, m), 8.37(1H, s), 10.29(1H, s), 10.48(1H, s). 170 δ 1.14(3H, t, J = 7.3Hz), 2.72(2H, q, J = 7.3Hz), 7.33-7.39(2H, m), 7.53-7.64(3H, m), 7.67-7.72(1H, m), 7.76(1H, d, J = 7.8Hz), 7.82(1H, s), 7.98(1H, d, J = 8.8Hz), 8.32(1H, s), 10.30 (1H, s), 10.65(1H, s). 171 δ 1.13(3H, t, J = 7.3Hz), 2.71(2H, q, J = 7.3Hz), 7.52-7.63(5H, m), 7.78(1H, d, J = 7.8Hz), 7.97-8.01(3H, m), 8.07-8.09(1H, m), 8.37(1H, d, J = 2.0Hz), 10.28(1H, s), 10.48(1H, s). 172 δ 1.13(3H, t, J = 7.3Hz), 2.71(2H, q, J = 7.3Hz), 7.33-7.39(2H, m), 7.54-7.63(3H, m), 7.67-7.72(1H, m), 7.78(1H, d, J = 7.8Hz), 7.97-8.00(2H, m), 8.33(1H, s), 10.30(1H, s), 10.66(1H, s). 173 δ 1.13(3H, t, J = 7.3Hz), 2.72(2H, q, J = 7.3Hz), 7.57-7.64(2H, m), 7.83(1H, d, J = 7.8Hz), 7.98(1H, s), 8.10(1H, d, J = 7.8Hz), 8.24(2H, d, J = 8.8Hz), 8.37(1H, s), 8.40(2H, d, J = 8.8Hz), 10.32(1H, s), 10.81(1H, s). -
[Table 6-8] Compound No. 1H-NMR (DMSO-d6, ppm) 174 δ 1.13(3H, t, J = 7.3Hz), 2.71(2H, q, J = 7.3Hz), 7.56-7.63(2H, m), 7.82(1H, d, J = 7.8Hz), 7.98(1H, s), 8.04-8.10(3H, m), 8.15(2H, d, J = 8.3Hz), 8.36(1H, s), 10.31(1H, s), 10.72(1H, s). 175 δ 0.85(3H, t, J = 7.3Hz), 1.49-1.59(2H, m), 2.30(3H, s), 2.65(2H, t, J = 6.8Hz), 7.40(1H, s), 7.47(1H, s), 7.58(1H, t, J = 7.8Hz), 7.79(1H, d, J = 7.8Hz), 8.08(1H, s), 8.22-8.25(2H, m), 8.36-8.41(3H, m), 10.03(1H, s), 10.79(1H, s). 176 δ 1.18(6H, d, J = 6.8Hz), 2.29(3H, s), 3.23(1H, septet, J = 6.8Hz), 7.41(1H, s), 7.47(1H, s), 7.52-7.63(4H, m), 7.75(1H, d, J = 7.8Hz), 7.99-8.01(2H, m), 8.06-8.09(1H, m), 8.36(1H, t, J = 2.0Hz), 10.00(1H, s), 10.48(1H, s). 177 δ 1.17(6H, d, J = 6.8Hz), 2.30(3H, s), 3.24(1H, septet, J = 6.8Hz), 7.28-7.41(3H, m), 7.47(1H, s), 7.55-7.63(2H, m), 7.65-7.78(2H, m), 7.99(1H. d, J = 7.8Hz), 8.33(1H, s), 10.02(1H, s), 10.66(1H, s). 178 δ 0.85(3H, t, J = 7.3Hz), 1.47-1.60(2H, m), 2.70(2H, t, J = 7.3Hz), 7.53-7.63(5H, m), 7.75(1H, d, J = 7.8Hz), 7.83(1H, d, J = 2.0Hz), 7.98-8.01(2H, m), 8.08(1H, d, J = 7.8Hz), 8.36(1H, s), 10.29 (1H, s), 10.49(1H, s). 179 δ 0.85(3H, t, J = 7.3Hz), 1.50-1.60(2H, m), 2.69(2H, t, J = 6.8Hz), 7.29-7.40(2H, m), 7.53-7.62(3H, m), 7.67-7.76(2H, m), 7.83(1H, d, J = 2.0Hz), 7.98(1H, d, J = 7.8Hz), 8.32(1H, s), 10.31(1H, s), 10.66(1H, s). 180 δ 0.85(3H, t, J = 7.3Hz), 1.50-1.58(2H, m), 2.70(2H, t, J = 7.8Hz), 7.57-7.63(2H, m), 7.78-7.84(2H, m), 8.09(1H, d, J = 7.8Hz), 8.18-8.24(2H, m), 8.35-8.41(3H, m), 10.32(1H, s), 10.80(1H, s). 181 δ 0.85(3H, t, J = 7.3Hz), 1.50-1.60(2H, m), 2.69(2H, t, J = 7.3Hz), 7.56-7.62(2H, m), 7.79 (1H, d, J = 7.8Hz), 7.83(1H, d, J = 2.0Hz), 8.04-8.09(3H, m), 8.15(2H, d, J = 8.8Hz), 8.35(1H, s), 10.31(1H, s), 10.72(1H, s). 182 δ 0.84(3H, t, J = 7.3Hz), 1.49-1.59(2H, m), 2.68(2H, t, J = 7.3Hz), 7.53-7.63(5H, m), 7.77(1H, d, J = 7.8Hz), 7.97-8.01(3H, m), 8.08(1H, d, J = 7.8Hz), 8.37(1H, s), 10.29(1H, s), 10.49(1H, s). 183 δ 0.84(3H, t, J = 7.3Hz), 1.49-1.59(2H, m), 2.67(2H, t. J = 7.3Hz), 7.28-7.40(2H, m), 7.51-7.63(3H, m), 7.68-7.72(1H, m), 7.77(1H, d, J = 8.3Hz), 7.97-8.00(2H, m), 8.33(1H, s), 10.31(1H, s), 10.67(1H, s). 184 δ 0.84(3H, t, J = 7.3Hz), 1.49-1.59(2H, m), 2.68(2H, t, J = 6.8Hz), 7.57-7.62(2H, m), 7.82(1H, d, J = 7.8Hz), 7.98(1H, d, J = 2.0Hz), 8.08-8.10(1H, m), 8.15-8.41(5H, m), 10.32(1H, s), 10.80(1H, s). 185 δ 0.84(3H, t, J = 7.3Hz), 1.49-1.57(2H, m), 2.68(2H, broad), 7.56-7.61(2H, m), 7.81(1H, d, J = 7.8Hz), 7.98(1H, s), 8.05(2H, d, J = 8.3Hz), 8.09(1H, s), 8.15(2H, d, J = 8.3Hz), 8.35(1H, s). 10.31(1H, s), 10.72(1H, s). 186 δ 0.84(3H, t, J = 7.3Hz), 1.49-1.57(2H, m), 2.68(2H, t, J = 6.8Hz), 7.56-7.61(2H, m), 7.80(1H, d, J = 7.8Hz), 7.94(2H, d, J = 8.3Hz), 7.98(1H, s), 8.09(1H, d, J = 7.8Hz), 8.20(2H, d, J = 8.3Hz), 8.36(1H, s), 10.31(1H, s), 10.71(1H, s). 187 δ 0.83(3H, t, J = 7.3Hz), 1.21-1.31(2H, m), 1.47-1.55(2H, m), 2.72(2H, t, J = 7.8Hz), 7.53-.63(5H, m), 7.70-7.75(2H, m), 7.99-8.01(2H, m), 8.06-8.09(1H, m), 8.37(1H, t, J = 2.0Hz), 10.27(1H, s), 10.49(1H, s). 188 δ 0.83(3H, t, J = 7.3Hz), 1.21-1.31(2H, m), 1.47-1.55(2H, m), 2.72(2H, t, J = 7.8Hz), 7.33-7.40(2H, m), 7.53-7.63(3H, m), 7.67-7.75(3H, m), 7.98(1H, d. J = 7.8Hz), 8.32(1H, s), 10.29(1H, s), 10.66(1H, s). 189 δ 0.83(3H, t, J = 7.3Hz), 1.21-1.31(2H, m), 1.47-1.55(2H, m), 2.72(2H, t, J = 7.3Hz), 7.52-7.63(5H, m), 7.75(1H, d, J = 7.8Hz), 7.82(1H, d, J = 1.5Hz), 7.99-8.01(2H, m), 8.08(1H, dd, J = 1.5,7.8Hz). 8.37(1H, t, J = 1.5Hz), 10.29(1H, s). 10,49(1H, s). 190 δ 0.83(3H, t, J = 7.3Hz), 1.21-1.31(2H, m), 1.47-1.55(2H, m), 2.71(2H, t, J = 7.3Hz), 7.28-7.37(2H, m), 7.53-7.62(3H, m), 7.72(1H, t, J = 7.3Hz), 7.75(1H, d, J = 7.8Hz), 7.82(1H. s), 7.98(1H, d, J = 7.8Hz), 8.62(1H, s), 10.31(1H, s), 10.66(1H. s). 191 δ 0.82(3H, t, J = 7.3Hz), 1.22-1.30(2H, m), 1.46-1.54(2H, m), 2.70(2H, t, J = 7.8Hz), 7.53-7.63(5H, m), 7.78(1H, d, J = 7.8Hz), 7.93-8.02(3H, m), 8.07-8.09(1H. m), 8.37(1H, s), 10.29 (1H, s), 10.49(1H, s). 192 δ 0.83(3H, t, J = 7.3Hz), 1.21-1.31(2H, m), 1.47-1.55(2H, m), 2.71(2H, t, J = 7.8Hz), 7.28-7.40(2H, m), 7.55-7.65(3H, m), 7.69-7.73(1H, m), 7.79(1H, d, J = 7.8Hz), 7.98-8.02(2H, m), 8.35(1H, s), 10.33(1H, s), 10.68(1H, s). 193 δ 0.75(3H, t, J = 7.3Hz), 1.18(3H, d, J = 6.8Hz), 1.55-1.60(2H, m), 3.00-3.05(1H, m), 7.49-7.67(5H, m), 7.72-7.77(2H, m), 7.99-8.02(2H, m), 8.09(1H, d, J = 7.8Hz), 8.36(1H, s), 10.29( 1H, s). 10.49(1H, s). -
[Table 6-9] Compound No. 1H-NMR (DMSO-d6, ppm) 194 δ 0.75(3H, t, J = 7.3Hz), 1.17(3H, d, J = 6.8Hz), 1.55-1.60(2H, m), 2.98-3.04(1H, m), 7.52-7.63(5H, m), 7.77(1H, d, J = 8.3Hz), 7.84(1H, s), 7.99-8.10(3H, m), 8.36(1H, s), 10.30(1H, s), 10.49(1H, s). 195 δ 0.74(3H, t, J = 7.3Hz), 1.17(3H, d, J = 6.8Hz), 1.55-1.63(2H, m), 2.98-3.04(1H, m), 7.33-7.40(2H, m), 7.52-7.63(3H, m), 7.67-7.77(2H, m), 7.83(1H, d, J = 1.5Hz), 7.99(1H, d, J = 8.3Hz), 8.32(1H, s), 10.32(1H, s), 10.66(1H, s). 196 δ 0.74(3H, t, J = 6.8Hz), 1.15(3H, d, J = 6.8Hz), 1.53-1.64(2H, m), 2.94-3.04(1H, m), 7.51-7.63(5H, m), 7.79(1H, d, J = 7.3Hz), 7.98-8.02(3H, m), 8.09(1H, dd, J = 1.5,7.8Hz), 8.37(1H, s), 10.30(1H, s), 10.50(1H, s). 197 δ 7.33-7.41(2H, m), 7.56-7.64(2H, m), 7.68-7.73(2H, m), 7.93-8.03(2H, m), 8.38-8.40(1H, m), 8.45(1H, d, J = 2.0Hz), 10.72(1H, s), 10.98(1H, s). 198 δ 2.50(3H, s), 7.39(1H, s), 7.48-7.63(4H, m), 7.73(1H, s), 7.77(1H, d, J = 7.8Hz), 7.99-8.01(2H, m), 8.08(1H, d, J = 7.8Hz), 8.35(1H, s), 10.36(1H, s), 10.50(1H, s). 199 δ 2.50(3H, s), 7.33-7.39(3H, m), 7.53-7.63(2H, m), 7.67-7.77(3H, m), 7.98(1H, d, J = 7.8Hz), 8.30(1H, s), 10.38(1H, s), 10.67(1H, s). 200 δ 2.81(3H, s), 7.53-7.64(4H, m), 7.75(1H, d, J = 8.3Hz), 7.99-8.01(2H, m), 8.08-8.11(2H, m), 8.25(1H, d, J = 2.0Hz), 8.40(1H, t, J = 2.0Hz), 10.52(1H, s), 10.61(1H, s). 201 δ 3.40(3H, s), 7.33-7.40(2H, m), 7.56-7.63(2H, m), 7.67-7.78(2H, m), 7.99(1H, d, J = 8.3Hz), 8.17(1H, d, J = 1.5Hz), 8.35(1H, s), 8.39(1H, d, J = 1.5Hz), 10.63(1H, s), 10.69(1H, s). 202 δ 3.40(3H, s), 7.57-7.62(2H, m), 7.79(1H, d, J = 7.8Hz), 7.96(1H, dd, J = 1.5,8.3Hz), 8.12(1H, dd, J = 1 .5,8.3Hz), 8.17(1H, d, J = 2.0Hz), 8.32(1H, d, J = 2.0Hz), 8.40(1H, d, J = 2.0Hz), 8.54-8.56(1H, m), 10.65(1H, s), 10.92(1H, s). 203 δ 3.40(3H, s), 7.53-7.63(4H, m), 7.78(1H, d, J = 7.8Hz), 7.98-8.01(2H, m), 8.07-8.10(1H, m), 8.21(1H, s), 8.39(1H, s), 8.48(1H, d, J = 1.5Hz), 10.51(1H, s), 10.63(1H, s). 204 δ 3.39(3H, s), 7.33-7.40(2H, m), 7.56-7.63(2H, m), 7.68-7.72(1H, m), 7.78(1H, d, J = 7.8Hz), 8.00(1H, d, J = 7.8Hz), 8.21(1H, d, J = 1.5Hz), 8.35(1H, s), 8.48(1H, d, J = 1.5Hz), 10.66(1H, s), 10.69(1 H, s). 205 δ 3.39(3H, s), 7.36-7.42(2H, m), 7.58(1H, t, J = 7.8Hz), 7.78(1H, d, J = 7.8Hz), 8.06-8.10(3H, m), 8.21(1H, s), 8.36(1H, s), 8.48(1H, s), 10.52(1H, s), 10.63(1H, s). 206 δ 3.39(3H, s), 7.61(1H, t, J = 7.8Hz), 7.82(1H, d, J = 7.8Hz), 8.09(1H, d, J = 7.8Hz), 8.20-8.24(3H, m), 8.37-8.41(3H, m), 8.48(1H, s), 10.67(1H, s), 10.83(1H, s). 207 δ 3.39(3H, s), 7.60(1H, t, J = 7.8Hz), 7.81(1H, d, J = 7.8Hz), 7.97-8.10(3H, m), 8.14-8.21(3H, m), 8.37(1H, t, J = 2.0Hz), 8,48(1H, d, J = 2.0Hz), 10.65(1H, s), 10.74(1H, s). 208 δ 3.39(3H, s), 7.57-7.62(2H, m), 7.80(1H, d, J = 7.8Hz), 7.96(1H, dd, J = 1.5,7.8Hz), 8.11 (1H, dd, J = 1.5,7.8Hz), 8.20(1H, s), 8.31(1H, s), 8.51(1H, s), 8.55(1H, dd, J = 1.5,4.9Hz), 10.68(1H, s), 10.92(1H, s). 209 δ 1.96(3H, s), 3.84(2H, broad), 7.53-7.63(4H, m), 7.73(1H, d, J = 7.8Hz), 7.89(1H, s), 7.99-8.01(2H, m), 8.07(1H, dd, J = 1.5,7.8Hz), 8.19(1H, s), 8.33(1H, t, J = 2.0Hz), 10.43(1H, s), 10.49(1H, s). 210 δ 7.53-7.64(4H, m), 7.81(1H, d, J = 7.8Hz), 8.00-8.05(3H, m), 8.11(1H, d, J = 7.8Hz), 8.31(1H, d, J = 1.5Hz), 8.41(1H, s), 10.52(1H, s), 10.93(1H, s). 211 δ 2.29(6H, s), 7.47(2H, s), 7.50-7.62(4H, m), 7.75(1H, d, J = 7.8Hz), 7.97-8.00(2H, m), 8.05(1H, dd, J = 1.5,7.8Hz), 8.36(1H, s), 10.01(1H, s), 10.46(1H, s). 212 δ 2.30 (6H, s), 7.45 (2H, s), 7.51-7.63 (4H, m), 7.76 (1H, d, J =7.8Hz), 7.98-8.07 (3H, m), 8.37 (1H, d, J =2.0Hz), 9.99 (1H, s), 10.48 (1H, s). 255 δ 7.25-7.29(2H, m), 7.54-7.65(2H, m), 7.78(1H, d, J = 7.8Hz), 7.92-7.95(1H, m), 8.03(2H, s), 8.30(1H, s), 10.58(1H, s), 11.05(1H, s). -
[Table 6-10] Compound No. 1H-NMR (DMSO-d6, ppm) 256 δ 7.53-7.63(4H, m), 7.78(1H, d, J = 7.3Hz), 7.99-8.01 (2H, m), 8.06-8.09(1H, m), 8.17(2H, s), 8.38(1H, s), 10.50(1H, s), 10.55(1H, s). 257 δ 7.25-7.29(2H, m), 7.55-7.63(2H, m), 7.79(1H, d, J = 7.3Hz), 7.94(1H, d, J = 8.3Hz), 8.17(2H, s), 8.30(1H, s), 10.60(1H, s), 11.05(1H, s). 258 (CDCl3) δ 7.45-7.61(4H, m), 7.76(1H, d, J=7.8Hz), 7.84-7.91(3H, m), 7.93(2H, s), 8.02(1H, s), 8.08(1H, d, J=6.8Hz), 8.31(1H, s). 259 (CDCl3) δ 7.22(1H, dd, J=7.8, 12.2Hz), 7.35(1H, t, J=7.8Hz), 7.52-7.60(2H, m), 7.77(1H, d, J=7.8Hz), 7.88(1H, s), 7.92(1H, s), 7.93(2H, d), 8.19(1H, dt, J=1.9, 7.8Hz), 8.33(1H, s), 8.64(1H, d, J=15.6Hz). 260 (CDCl3) δ 2.31(6H, s), 7.41(2H, s), 7.50-7.67(5H, m), 7.71(1H, d, J=7.8Hz), 7.87-7.90(3H, m), 8.07(1H, s), 8.31(1H, s). 261 (CDCl3) δ 2.33(6H, s), 7.20-7.25(1H, m), 7.35(1H, t, J=7.3Hz), 7.44(2H, s), 7.52-7.60 (3H, m), 7.73(1H, d, J=7.8Hz), 7.88(1H, dd, J=1.0, 7.8Hz), 8.18(1H, dt, J=2.0, 7.8Hz), 8.33 (1H, s), 8.63(1H, d, J=7.3Hz). 262 (CDCl3) δ 7.44-7.57(5H, m), 7.72(2H, s), 7.78(1H, d, J=7.8Hz), 8.00(1H, d, J=6.8Hz), 8.18(1H, d, J=8.3Hz), 8.34(1H, t, J=2.0Hz), 9.46(1H, s), 9.83(1H, s). 263 (CDCl3) δ 7.47-7.57(4H, m), 7.78(1H, d, J=7.8Hz), 7.93(2H, s), 7.99-8.01(2H, m), 8.18(1H, d, J=7.8Hz), 8.33(1H, t, J=2.0Hz), 9.27(1H, s), 9.65(1H, s). 266 δ 7.20-7.25(1H, m), 7.35(1H, t, J=7.8Hz), 7.53-7.60(2H, m), 7.76-7.79(2H, m), 7.95(2H, s), 7.96(1H, s), 8.19(1H, dt, J=2.0. 7.8Hz). 8.32(1H, s), 8.63(1H, d, J=15.7Hz). 276 (CDCl3) δ 7.56(1H, t, J = 7.8Hz), 7.71(1H, d, J = 7.8Hz), 7.75(1H, d, J = 7.8Hz), 7.87-7.90(3H, m), 8.04(1 H, d, J = 7.8Hz), 8.28(2H, s), 8.42(1H, dd, J = 1.0, 7.3Hz), 8.46(1H, s), 8.76(1H, t, J = 2.0Hz). 284 (CDCl3) δ7.03(2H, t, J=7.8Hz), 7.42-7.49(1H, m), 7.54(1H. t, J=7.8Hz), 7.78(1H, d, J=7.8Hz), 7.81(1H, s), 7.87-7.92(2H, m), 7.93(2H. s). 8.28(1H, t, J=2.0Hz). 285 δ 6.86(1H, d, J = 8.8Hz), 7.24(1H, t, J = 7.8Hz), 7.30-7.32(2H, m), 7.47(1H, t, J = 7.8Hz), 7.77(1H, d, J = 7.8Hz), 7.93(2H, s), 8.14(1H, d, J = 7.3Hz), 8.31(1H, s), 9.32(1H, s), 9.46(1H, s). 286 δ 2.17(3H, s), 7.40(1H, t, J = 7.8Hz), 7.49(1H, t, J = 7.8Hz), 7.80(1H, d, J = 7.8Hz), 7.78 (1H, d, J = 7.8Hz), 7.94-7.95(3H, m). 8.06(1H, s), 8.16(1H, d, J = 7.8Hz), 8.31(1H, s), 9.50 (1H, s), 9.58(1H, s), 9.79(1H, s). 287 δ 3.00(3H, s), 7.42(1H, t, J = 7.8Hz), 7.50(1H, t, J = 7.8Hz), 7.48(1H, s), 7.74(1H, d, J = 7.8Hz), 7.79(1H, d, J = 7.8Hz), 7.88(1H, t, J = 2.0Hz), 7.93(2H, s), 8.17(1H, d, J = 7.8Hz), 8.29(1H, t, J = 2.0Hz), 9.37(1H, s), 9.49(1H, s), 9.72(1H, s). 288 (CDCl3) δ 7.51(1H, t, J = 7.8Hz), 7.69(1H, d, J = 7.8Hz), 7.86-7.91(3H, m), 7.95(2H, s), 8.07(1H, s), 8.39(1H, s), 8.53-8.55(1H, m), 8.90(1H, s). 289 (CDCl3) δ 7.54(1H, t, J = 8.3Hz), 7.80(1H, d, J = 7.8Hz), 7.94(2H, s), 8.02(1H, d, J = 8.3Hz), 8.26-8.27(2H, m), 8.52(1H, d, J = 8.3Hz), 8.74(1H, s), 8.87(1H, s), 10.56(1H, s). 290 δ 2.68(3H, s), 7.52(1H, t, J = 7.8Hz), 7.81(1H, d, J = 7.8Hz), 7.93(2H, s), 8.03(2H, s), 8.07(1H, s), 8.24(1H, d. J = 7.8Hz), 8.29(1H, s), 9.34(1H, s), 10.13(1H, s). 291 (CDCl3) δ 4.17(2H, s), 6.80-6.84(1H, m), 6.98(1H, dd, J = 7.8, 11.2Hz), 7.33(1H, dd, J = 2.9, 6.4Hz), 7.51(1H, t, J = 7.8Hz), 7.82(1H, d, J = 7.8Hz), 7.94(2H, s), 8.10(1H, d, J = 8.2Hz), 8.22(1H, s), 9.06(1H, d, J = 13.2Hz). 9.48(1H, s). 292 (CDCl3) δ 7.44(1H, dd, J = 8.8, 10.7Hz), 7.58(1H, t, J = 7.8Hz), 7.80(1H, d, J = 7.8Hz), 7.85(1H, s), 7.95(2H, s), 7.98(1H, d, J = 7.8Hz), 8.27(1H, s), 8.43-8.47(1H, m), 8.55(1H, d, J = 14.2Hz), 9.09(1H, dd, J = 3.0, 6.4Hz). 293 δ 2.97(3H, s), 7.16(1H, dd, J = 8.8, 10.8Hz), 7.49(1H, t, J = 7.8Hz), 7.51(1H, s), 7.83(1H, d, J = 7.8Hz), 7.90-7.93(1H, m), 7.94(2H, s), 8.10(1H, d, J = 7.8Hz), 8.24(1H, s), 9.15(1H, d, J = 11.2Hz), 9.38(1H, s), 9.58(1H, s). -
[Table 6-11] Compound No. 1H-NMR (DMSO-d6, ppm) 294 (CDCl3) δ 4.22(3H, s), 7.56(1H, t, J = 7.8Hz), 7.75(1H, t, J = 7.8Hz), 7.83(1H, s), 7.94(1H, s), 7.95(2H, s), 7.99-8.05(2H, m), 8.25(1H, s), 8.47(1H, d, J = 7.8Hz), 9.83(1H, s). 295 δ 4.06(3H, s), 7.52(1H, t, J = 7.3Hz), 7.73(1H, d, J = 8.3Hz), 7.82-7.88(2H, m), 7.89(1H, d, J = 8.3Hz), 7.93(2H, s), 8.25-8.29(2H, m), 9.48(1H, s), 10.23(1H, s). 296 (CDCI3) δ 216(3H, s), 7.14(1H, dd, J = 9.3, 11.2Hz), 7.52(1H, t, J = 7.8Hz), 7.80(1H, d, J = 7.8Hz), 7.94(2H, s), 7.96(1H, d, J = 2.9Hz), 8.01(1H, d, J = 7.8Hz), 8.13-8.16(1H, m), 8.27(1H, s), 8.86(1H, s), 8.90(1H, d, J = 14.2Hz), 9.00(1H, s). 306 (CDCI3) δ 7.52-7.58(2H, m), 7.77(1H, d, J = 7.8Hz), 7.90(1H, s), 7.94(2H, s), 7.95(1H, d, J =7.8Hz), 8.01-8.03(1H, m), 8.31(1H, d, J = 7.8Hz), 8.47(1H, s), 8.65(1H, dd, J = 1.0, 4.9Hz), 10.25(1H, s). 307 (CDCl3) δ 7.57(1H, t, J = 7.8Hz), 7.73-7.77(3H, m), 7.84(1H, s), 7.89(2H, s), 8.05(1H, d, J = 7.8Hz), 8.26(1H, s), 8.32(1H, s), 8.81(1H, s), 8.83(1H, s). 309 (CDCl3) δ 7.44(1H, dd, J=4.8, 7.8Hz), 7.56(1H, t, J=7.8Hz), 7.80(1H, d, J=7.8Hz), 7.86(1H, s). 7.92(1H, d, J=7.3Hz), 7.95(2H, s), 8.23(1H, dd, J=20., 7.9Hz), 8.30(1H, s), 8.41(1H, s). 8.55 (1H, dd, J=20, 4.5Hz). 310 (CDCl3) δ 7.46(1H, d, J = 8.3Hz), 7.55(1H, t, J = 8.3Hz), 7.74(1H, d, J = 8.3Hz), 7.88(3H, s), 8.03(1H, d, J = 7.8Hz), 8.18(1H, dd, J = 3.0, 8.2Hz), 8.24(1H, s), 8.41(1H, s), 8.90(1H, d, J = 2.4Hz). 312 (CDCl3) δ 7.57(1H, t, J = 7.8Hz), 7.70(2H, s). 7.75(1H, d, J = 7.8Hz), 7.83(1H, s), 7.88(2H, s), 8.04(1H, d, J = 7.8Hz), 8.21(1H, s), 8.47(1H, s). 313 (CDCl3) δ 7.33(1H, t, J = 7.8Hz), 7.46(1H, d, J = 8.3Hz), 7.60(1H, s), 7.76(1H, s), 7.80(1H, d, J = 7.8Hz), 7.95(2H, s), 8.18-8.23(2H, m), 8.40(1H, s). 314 (CDCl3) δ 262(3H, s), 7.29(1H. s), 7.56(1H, t, J = 7.8Hz), 7.77-7.79(2H, m), 7.91(1H, s), 7.94(2H, s), 8.16(1H, d, J = 7.8Hz), 8.29(1H, s), 8.48(1H, s). 315 (CDCl3) δ 7.47-7.59(3H, m), 7.80(1H, d, J = 7.8Hz), 7.93(1H, s), 7.94(2H, s), 8.26(1H, s), 8.34(1H, d, J = 6.5Hz). 8.47(1H, t, J = 2.0Hz), 8.52-8.55(1H, m), 13.91(1H, s). 316 (CDCl3) δ 7.59(1H, t, J = 7.8Hz), 7.79(1H, d, J = 7.8Hz), 7.84(1H, s), 7.95(2H, s), 8.04 (1H, d, J = 7.8Hz), 8.41(1H, t, J = 2.0Hz), 8.63(1H, t, J = 2.5Hz), 8.86(1H, d, J = 2.4Hz), 9.54(1H, d, J = 1.5Hz), 9.87(1H, s). 317 (CDCl3) δ 3.93(3H, s), 7.53(1H, t, J = 7.8Hz), 7.74(1H, d, J = 7.8Hz), 7.84(1H, s), 7.87(1H, d, J = 7.8Hz), 7.94(2H, s), 8.03(1H, s). 8.26(1H, t, J = 2.0Hz), 8.48(1H, s). 318 (CDCl3) δ 4.02(3H, s), 7.53(1H, t, J = 7.8Hz), 7.45(1H, d, J = 7.8Hz), 7.80(1H, d, J = 7.8Hz), 7.85(1H, s), 7.89(1H, s), 7.94(2H, s), 8.05(1H, s), 8.24(1H, s). 319 (CDCl3) δ 4.10(3H, s), 7.53(1H, t, J = 7.8Hz), 7.67(1H, s), 7.76(1H, d, J = 7.8Hz), 7.70-7.86(3H, m), 7.94(2H, s), 8.21(1H, s). 320 (CDCl3) δ 1.94-2.04(2H, m), 2.17-2.22(1H, m), 237-2.42(1H, m), 3.95-4.00(1H, m), 4.05-4.09(1H, m), 4.49(1H, dd, J = 5.9, 8.3Hz), 7.50(1H, t, J = 7.8Hz), 7.72(1H, d, J = 7.8Hz), 7.83(1H, dd, J = 2.0, 7.8Hz), 7.87(1H, s), 7.94(2H, s), 8.23(1H, t, J = 2.0Hz), 8.67(1H, s). 321 (CDCl3) δ 7.51-7.53(3H, m), 7.57(1H, t, J = 8.3Hz), 7.76(1H, d, J = 7.3Hz), 7.83(1H, s), 7.95(2H, s), 8.01-8.07(3H, m), 8.23(1H, s), 8.38(1H, s), 9.51(1H, s). 327 (CDCl3) δ 7.45-7.61(4H, m), 7.77(1H, d, J = 7.8Hz), 7.84-7.91(3H, m), 7.97-8.18(4H, m), 8.31(1H, s). 328 (CDCl3) δ 7.24(1H, d, J = 7.8Hz), 7.35(1H, t, J = 7.8Hz), 7.54-7.60(2H, m), 7.78(1H, d, J = 7.8Hz), 7.89(1H, s), 7.96(1H, d, J = 7.8Hz), 8.15-8.19(3H, m), 8.33(1H, s), 8.64(1H, d, J = 15.6Hz). 329 (CDCl3) δ 7.44-7.57(4H, m), 7.70(2H, s), 7.78(1H, d, J=7.8Hz), 8.01(2H, d, J=6.8Hz), 8.17(1H, dd, J=1.0. 7.8Hz). 8.34(1H, t, J=2.0Hz), 9.45(1H, s), 9.81(1H, s). -
[Table 6-12] Compound No. 1H-NMR (DMSO-d6, ppm) 330 (CDCl3) δ 7.22(1H, dd, J=8.3, 12.2Hz), 7.34(1H, t, J=7.3Hz), 7.52-7.67(2H, m), 7.72(2H, s), 7.76(1H, d, J=7.9Hz), 7.90(1H, s), 7.92(1H, s), 8.18(1H, dt, J=1.4, 7.8Hz), 8.33(1H, t, J=2.0Hz), 8.64(1H, d, J=16.6Hz). 331 (CDCl3) δ 7.44(1H, dd, J=4.4, 7.8Hz), 7.57(1H, t, J=7.8Hz), 7.73(2H, s), 7.78(1H, d, J=7.8Hz), 7.84(1H, s), 7.90(1H, d, J=7.8Hz), 8.23(1H, dd, J=2.0, 7.8Hz), 8.29(1H, s), 8.41(1H, s), 8.55 (1H, dd, J=2.0, 4.9Hz). 332 δ 7.43-7.57(4H, m), 7.79(1H, d, J=7.8Hz), 7.92(2H, s), 8.00(2H, d, J=6.9Hz), 8.18(1H, d, J=8.3Hz), 8.35(1H, t, J=2.0Hz), 8.59(1H, s), 9.86(1H, s). 333 (CDCl3) δ 7.30-7.62(4H, m), 7.75(1H, d, J=7.8Hz), 7.84(1H, d, J=7.8Hz), 7.89-7.92(3H, m), 7.93(2H, s), 8.03(1H, s), 8.31(1H, s). 334 (CDCl3) δ 7.20-7.25(1H, m), 7.35(1H, t, J=6.3Hz), 7.54-7.58(2H, m), 7.79(1H, d, J=6.3Hz), 7.90-7.94(2H, m), 7.95(2H, s), 8.19(1H, t, J=8.3Hz), 8.33(1H, t, J=2.0Hz), 8.64(1H, d, J=16.1Hz). 335 (CDCl3) δ 7.45-7.61 (4H, m), 7.77-7.79 (1H, m), 7.87-7.91 (3H, m), 8.01 (1H, s), 8.07-8.10 (1 H, m), 8.15 (1H, s), 8.25 (1H, s), 8.38 (1H, s) 338 (CDCl3) δ 7.22(1H, t, J = 7.8Hz), 7.36(1H, t, J = 7.8Hz), 7.54-7.60(2H, m), 7.78(1H, d, J = 7.8Hz), 7.90(1H, d, J = 7.8Hz), 8.03-8.04(2H, m), 8.19(1H, t, J = 7.8Hz), 8.26(1H, s), 8.41(1H, s), 8.65(1H, d, J = 16.6Hz). 369 (CDCl3) δ 7.46(1H, dd, J = 4.4, 7.8Hz), 7.59(1H, t, J = 8.3Hz), 7.81(1H, d, J = 8.3Hz), 7.89-7.92(1H, m), 8.04(2H, s), 8.24(1H, dd, J = 2.0, 7.8Hz), 8.27(1H, s), 8.35(1H, d, J = 13.7Hz), 8.42(1H, s), 8.56(1H, dd, J = 1.4, 4.4Hz). 375 δ 7.25(1H, d, J = 8.3Hz), 7.27(1H, d, J = 7.8Hz), 7.56-7.64(2H, m), 7.79(1H, d, J = 7.8Hz), 7.94(1H, d, J = 8.3Hz), 8.32(1H, s), 8.42(2H, s), 10.87(1H, s), 11.05(1H, s). 376 δ 7.53-7.64(4H, m), 7.80(1H, d, J = 7.8Hz), 7.99-8.01(2H, m), 8.09(1H, dd, J = 1.5,7.8Hz), 8.41(1H, d, J = 1.5Hz), 8.54(2H, s), 10.52(1H, s), 10.83(1H. s). 377 δ 7.19-7.30(2H, m), 7.57-7.66(2H, m), 7.81(1H, d, J = 7.8Hz), 7.95(1H, dd, J = 1.5,7.8Hz), 8.33(1H, t, J = 1.5Hz), 8.53(2H, s), 10.89(1H, s), 11.08(1H, s). 378 (CDCI3) δ 7.21-7.23(1H, m), 7.36(1H, t, J=6.9Hz), 7.55-7.59(2H, m), 7.79(1H, d, J=8.3Hz), 7.84(1H, d, J=8.0Hz), 8.05(2H, s), 8.17-8.21(2H, m), 8.43(1H, t, J=2.0Hz), 8.65(1H, d, J=6.9Hz). 379 (CDCI3) δ 7.46-7.63(4H, m), 7.77(1H, d, J=7.8Hz), 7.84-7.91(3H, m), 8.00(1H, s), 8.07(2H, s), 8.14(1H, s), 8.40(1H, t, J=2.0Hz). 380 (CDCl3) δ 7.52-7.63(4H, m), 7.77(1H, d, J = 7.8Hz), 7.89(1H, s), 7.90(2H, d, J = 7.8Hz), 7.99(1H, s), 8.03(1H, s), 8.26(2H, s), 8.39(1H, t J = 2.0Hz). 383 (CDCl3) δ 7.21(1H, d, J = 8.3Hz), 7.36(1H, t, J = 7.8Hz), 7.55-7.61(2H, m), 7.78(1H, d, J = 7.8Hz), 7.90(1H, d, J = 8.3Hz), 8.02(1H, s), 8.19(1H, dt, J = 1.9, 8.3Hz), 8.27(2H, s), 8.41(1H, s), 8.65(1H, d, J = 16.6Hz). 414 (CDCl3) δ 7.44(1H, dd, J = 4.9, 7.8Hz), 7.59(1H, t, J = 8.3Hz), 7.81(1H, d, J = 7.8Hz), 7.89(1H, d, J = 8.3Hz), 8.04(1H, s), 8.23(1H, dd, J = 1.9, 7.8Hz), 8.27(2H, s), 8.37(1H, s), 8.43(1H, s), 8.55(1H, dd, J = 1.9, 4.3Hz). 460 δ 7.25(1H, d, J = 8.3Hz), 7.27(1H, d, J = 7.8Hz), 7.56-7.64(2H, m), 7.79(1H, d, J = 7.8Hz), 7.94(1H, d, J = 8.3Hz), 8.32(1H, s), 8.42(2H, s), 10.87(1H, s), 11.05(1H, s). 461 (CDCl3) δ 2.47 (3H, s), 7.51-7.62 (5H, m), 7.75 (1H, d, J =7.8Hz), 7.89-7.93 (4H, m), 8.00 (1H, broad-s), 8.35 (1H, t, J =2.0Hz). 462 (CDCl3) δ 2.47 (3H, s), 7.20-7.23 (1H, m), 7.36 (1H, t, J =7.8Hz), 7.55-7.60 (3H, m), 7.76 (1H, d, J =7.8Hz), 7.89 (1H, s), 7.92 (1H, s), 8.18-8.22 (1H, m), 8.39 (1H, s), 8.62 (1H, broad-s). 463 (CDCl3) δ 2.27 (3H, s), 2.41 (3H, s), 6.59 (1H, septet, J =6.4Hz), 6.72 (1H, s), 7.49-7.61 (5H, m), 7.70 (1H, d, J =7.8Hz), 7.83-7.89 (3H, m), 8.05 (1H, broad-s), 8.33 (1H, t, J =1.5Hz). -
[Table 6-13] Compound No. 1H-NMR (DMSO-d6, ppm) 464 (CDCl3) δ 2.38 (3H, s), 6.34 (1H, septet, J =6.4Hz), 6.87 (1H, s), 7.50-7.63 (5H, m), 7.72 (1H, d, J =7.8Hz), 7.88-7.90 (3H, m), 7.99 (1H, brs), 8.31 (1H, broad-s). 465 (CDCl3) δ 2.37 (3H, s), 6.36 (1H, septet, J =5.9Hz), 6.87 (1H, s), 7.50-7.61 (4H, m), 7.72-7.73 (2H, m), 7.88-7.90 (3H, m), 8.06 (1H, broad-s), 8.32 (1H, s). 466 (CDCl3) δ 2.39 (3H, s), 6.36 (1H, septet, J =5.9Hz), 6.89 (1H, s), 7.20-7.25 (1H, m), 7.35 (1H, t, J =6.8Hz), 7.52-7.60 (2H, m), 7.70 (1H, broad-s), 7.75 (1H, d, J =7.8Hz), 7.89 (1H, d, J =7.8Hz), 8.17-8.21 (1H, m), 8.36 (1H, s), 8.64 (1H, broad-d, J =16.1Hz). 467 (CDCl3) δ 2.53 (3H, s), 6.35 (1H, septet, J =5.9Hz), 6.83 (1H, s), 7.49-7.61 (4H, m), 7.66 (1H, s), 7.74 (1H, d, J =8.3Hz), 7.88-7.92 (3H, m), 8.32 (1H, broad-s), 8.33 (1H, t J =1.9Hz). 601 δ 2.34(6H, s), 7.37(1H, t, J = 7.8Hz), 7.45(2H, s), 7.53-7.65(4H, m), 7.77-7.82 (1H, m), 8.00-8.02(2H, m), 10.10(1H, s), 10.29(1H, s). 602 δ 2.36 (6H, s), 2.56 (3H, s), 7.29-7.43 (7H, m), 7.55-7.57 (1H, m), 7.75-7.78 (1H, m), 7.84-7.88 (1H, m), 8.64-8.66 (1H, m). 603 δ 2.37 (6H, s), 2.46 (3H, s), 7.34-7.42 (5H, m), 7.69-7.85 (4H, m), 8.11 (1H, s), 8.59-8.63 (1H, s). 604 δ 2.38 (6H, s), 2.45 (3H, s), 7.33-7.38 (5H, m), 7.78-7.85 (4H, m), 8.10 (1H, s), 8.61-8.65 (1H, m). 605 δ 2.34 (6H, s), 7.39 (1H, t, J =7.4Hz), 7.44 (2H, s), 7.50-7.54 (1H, m), 7.76-7.80 (2H, m), 7.88 (1H, t J =7.4Hz), 8.12 (1H, t, J =7.4Hz), 8.20 (1H, d, J =1.0Hz), 10.12 (1H, s), 10.73 (1H, s). 606 δ 2.35 (6H, s), 7.40 (1H, t, J =7.8Hz), 7.45 (2H, s), 7.59-7.62 (1H, m), 7.82-7.90 (2H, m), 8.44-8.50 (2H, m), 8.86 (1H, d, J =2.0Hz), 10.12 (1H, s), 10.72 (1H, s). 607 δ 2.34 (6H, s), 7.40 (1H, t, J =7.8Hz), 7.45 (2H, s), 7.57-7.62 (1H, m), 7.81-7.85 (1H, m), 8.22-8.25 (2H, m), 8.39-8.42 (2H, m), 10.12 (1H, s), 10.66 (1H, s). 609 δ 2.34 (6H, s), 7.39 (1H, t, J =6.9Hz), 7.45 (2H, s), 7.58 (1H, t, J =6.9Hz), 7.82 (1H, t, J =6.9Hz), 8.06 (2H. d, J =8.8Hz), 8.15 (2H, d, J =8.8Hz), 10.12 (1H, s), 10.58 (1H, s). 610 δ 234(6H, s), 7.33-7.40(3H, m), 7.45(2H, s), 7.52-7.56(1H, m), 7.59-7.65(1H, m), 7.72-7.77(1H, m), 8.00(1H, t, J = 7.8Hz), 10.12(1H, s), 10.35(1H, s). 611 δ 2.34 (6H, s), 7.38 (1H, t, J =7.6Hz), 7.45-7.65 (5H, m), 7.78-7.83 (2H, m), 7.87 (1H, d, J =7.6Hz), 10.10 (1H, s), 10.39 (1H, s). 612 δ 2.34 (6H, s), 7.35-7.45 (5H, m), 7.55-7.59 (1H, m), 7.77-7.81 (1H, m), 8.07-8.12 (2H, m), 10.09 (1 H. s). 10.32 (1H, s). 616 δ 234(6H, s), 7.22-7.27(1H, m), 7.38(1H, t, J = 7.8Hz), 7.46(2H, s), 7.50-7.55(3H, m), 7.95(1H, d, J = 7.8Hz), 7.99-8.03(1H, m), 10.12(1H, s), 10.50(1H, s). 618 δ 2.34 (6H, s), 7.39 (1H, t, J =7.7Hz), 7.45 (2H, s), 7.60 (1H, t, J =7.7Hz), 7.83 (1H, t, J =7.7Hz), 7.95 (2H, d, J =8.3Hz), 8.20 (2H, d, J =8.3Hz), 10.12 (1H, s), 10.56 (1H, s). 619 δ 2.34 (6H, s), 7.38 (1H, t, J =7.4Hz), 7.45 (2H, s), 7.55-7.60 (3H, m), 7.81 (1H, t, J =7.4Hz), 8.14 (2H, d, J =8.8Hz), 10.11 (1H, s), 10.40 (1H, s). 620 δ 2.34 (6H, s), 3.01 (6H, s), 6.77 (2H, d, J =9.0Hz), 7.33 (1H, t, J =7.0Hz), 7.45 (2H, s), 7.52 (1H, t, J =7.0Hz), 7.78 (1H, t, J =7.0Hz), 7.90 (2H, d, J =9.0Hz), 9.86 (1H, s), 10.07 (1H, s). 624 δ 234(6H, s), 7.23-7.28(2H, m), 7.38(1H, t, J = 7.8Hz), 7.45(2H, s), 7.52-7.64(2H, m), 8.05-8.10(1H, m), 10.13(1H, s), 10.88(1H, s). -
[Table 6-14] Compound No. 1H-NMR (DMSO-d6, ppm) 628 δ 2.34 (6H, s), 7.37-7.42(1H, m), 7.40 (2H, s), 7.55-7.58 (1H, m), 7.95-8.07 (2H, m), 8.21 (1H, dd, J =8.9,2.1 Hz), 8.30 (1 H, dd, J =8.9,2.1 Hz), 10.13 (1H, s), 10.75 (1 H, s). 629 δ 2.34 (6H, s), 7.39 (1H, t, J =7.4Hz), 7.45 (2H, s), 7.52 (1H, 7.4), 7.81 (1H, dd, J =8.3,2.7Hz), 7.88 (1 H, dd, J =8.3,5.6Hz), 8.10-8.16 (2H, m), 10.13 (1H, s), 10.75 (1 H, s). 630 δ 2.33 (6H, s), 7.34-7.38 (2H, m), 7.43 (2H, s), 7.51-7.54 (1H, m), 7.58-7.60 (1H, m), 7.67-7.71 (1H, m), 8.00-8.04 (1H, m), 10.10 (1H, s), 10.54 (1H, s). 631 δ 2.34 (6H, s), 7.37 (1H, t, J =7.9Hz), 7.45-7.47 (3H, m), 7.52-7.56 (1H, m), 7.65 (1H, dd, J =10.2,2.0Hz), 7.77 (1H, t, J =7.9Hz), 7.99-8.02 (1H, m), 10.11 (1H, s), 10.41 (1H, s). 633 δ 2.34 (6H, s), 7.40 (1H, t, J =8.1 Hz), 7.45 (2H, s), 7.55 (1H, t, J =6.5Hz), 7.92 (1H, d, J =8.1Hz), 8.10 (1H, t, J =6.5Hz), 8.32 (1H, t, J =8.1Hz), 8.43 (1H, s), 10.13 (1H, s), 10.84 (1H, s). 634 δ 2.34 (6H, s), 7.39 (1H, t, J =8.0Hz), 7.45 (2H, s), 7.51-7.55 (1H, m), 7.83 (1H, d, J =8.0Hz), 7.99 (1H, dd, J =7.7,2.2Hz), 8.12 (1H, t, J =7.7Hz), 8.30 (1H, d, J =2.2Hz), 10.13 (1H, s), 10.78 (1H, s). 638 δ 2.33 (6H, s), 7.37 (1H, t, J =8.1Hz), 7.44 (2H, s), 7.50-7.55 (2H, m), 8.03-8.07 (1H, m), 8.26-8.31 (1H, m), 8.41-8.42 (1H, m), 10.10 (1H, s), 10.54 (1H, s). 639 (CDCl3) δ 2.38 (6H, s), 7.38 (2H, s), 7.41-7.49 (2H, m), 7.80 (1H, broad-d, J =11.4Hz), 7.90-7.94 (1H, m), 8.32-8.35 (1H, m), 8.57-8.59 (1H, m), 8.62-8.65 (1H, m), 8.74 (1H, s). 648 δ 1.80-1.86 (2H, m), 2.05 (3H, s), 2.33-2.38 (8H, m), 3.99 (2H, t, J =5.1Hz), 7.29 (1H, t, J =7.4Hz), 7.44-7.48 (3H, m), 7.79 (1H, d, J =7.4Hz), 9.25 (1H, s), 10.04 (1H, s). 649 δ 2.29(6H, s), 7.45(2H, s), 7.54-7.66(3H, m), 7.77(1H, d, J =8.8Hz), 7.94(1H, dd, J =2.0,8.1Hz), 8.00-8.03(2H, m), 8.19(1H, d, J =2.0Hz), 10.10(1H, s), 10.29(1H, s). 650 δ 2.29(6H, s), 7.45(2H, s), 7.48-7.65(4H, m), 7.93-8.02(3H, m), 8.23(1 H, dd, J =2.4, 7.3Hz), 10.03(1H, s), 10.32(1H, s). 651 δ 2.29(6H, s), 7.45(2H, s), 7.54(1H, dd, J = 8.8,9.8Hz), 7.96-8.01(1H, m), 8.23(2H, d, J = 8.8Hz), 8.26(1H, dd, J = 2.4,8.8Hz), 8.40(2H, d, J = 8.8Hz), 10.05(1H, s), 10.70(1H, s). 652 δ 2.29(6H, s), 7.45(2H, s), 7.51-7.56(1H, m), 7.96-8.00(1H, m), 8.06(2H, d, J = 8.3Hz), 8.15(2H, d, J = 8.3Hz), 8.25(1H, dd, J = 2.0,7.3Hz), 10.05(1H, s), 10.61(1H, s). 653 δ 2.29(6H, s), 7.33-7.40(2H, m), 7.45(2H, s), 7.49-7.54(1H, m), 7.59-7.65(1H, m), 7.73-7.77(1H, m), 7.91-7.95(1H, m), 8.42(1H, d, J = 6.3Hz), 10.05(1H, s), 10.35(1H, s). 654 δ 2.29(6H, s), 7.37-7.45(4H, m), 7.51(1H, dd, J = 8.8,9.8Hz), 7.93-7.98(1H, m), 8.06-8.10(2H, m), 8.22(1H, dd, J = 2.0,7.3Hz), 10.03(1H, s), 10.37(1H, s). 655 δ 2.29(6H, s), 7.45(2H, s), 7.51-7.56(1H, m), 7.94-8.00(3H, m), 8.20(2H, d, J = 8.3Hz), 8.25(1H, dd, J = 2.0,7.3Hz), 10.05(1H, s), 10.59(1H, s). 656 δ 2.29(6H, s), 7.23-7.28(1H, m), 7.42-7.54(4H, m), 7.80-7.87(1H, m), 7.91-7.95(1H, m), 8.41(1H, d, J = 5.9Hz), 10.05(1H, s), 10.36(1 H, s). 657 δ 2.30(6H, s), 7.46(2H, s), 7.50-7.59(2H, m), 7.92-7.96(1H, m), 8.10(1H, dd, J = 2.0,7.3Hz), 8.52-8.56(2H, m), 10.07(1H, s), 10.73(1H, s). 658 δ 2.31(6H, s), 7.47(2H, s), 7.55-7.59(2H, m), 7.62-7.66(1H, m), 8.01-8.04(2H, m), 8.09(1H, s), 8.54(1H, s), 8.66(1H, s), 10.27(1H, s), 10.79(1H, s). 659 δ2.34(6H, s), 7.40(1H, t, J =9.3Hz), 7.45(2H, s), 7.53-7.64(3H, m), 7.97-8.05(3H, m), 8.14(1H, dd, J =2.9,6.3Hz), 10.03(1H, s), 10.48(1H, s). -
[Table 6-15] Compound No 1H-NMR (DMSO-d6, ppm) 660 δ 2.40(6H, s), 7.45(2H, s), 7.54-7.65(4H, m), 7.97-8.03(3H, m), 8.09(1H, d, J =2.4Hz), 10.20(1H, s), 10.56(1H, s). 661 δ 2.41(6H, s), 7.45(2H, s), 7.54-7.65(3H, m), 7.72(1H, d, J = 8.8Hz), 7.94-7.99(3H, m), 8.08(1H, d, J = 2.9Hz), 10.20(1H, s), 10.56(1H, s). 662 δ 2.44(6H, s), 7.45(2H, s), 7.53-7.65(3H, m), 7.79(1H, dd, J =2.4,8.3Hz), 7.90-7.98 (3H, m), 8.05(1H, d, J =2.4Hz), 10.15(1H, s), 10.53(1H, s). 663 δ 2.35(6H,s),7.32(1H,t,J=8.3),7.46(2H,s),7.54-7.77(4H,m),8.00(2H,dd,J=1.5,J=8.3), 10.3(1H,s),10.6(1H,s). 664 (CDCl3) δ 2.53(6H, s), 7.35(2H, s), 7.52-7.63(5H, m), 7.92(2H, d, J = 8.8Hz), 8.46(1H, d, J = 8.8Hz), 8.57(1H. s). 665 δ 234(6H, s), 7.37(1H, t, J = 7.8Hz), 7.44(2H, s), 7.53-7.65(4H, m), 7.77-7.81(1H, m), 7.99-8.02(2H, m), 10.09(1H, broad), 10.29(1H, broad). 668 δ 2.34(6H, s), 7.33-7.40(3H, m), 7.44(2H, s), 7.51-7.56(1H, m), 7.58-7.65(1H, m), 7.72-7.77(1H, m), 8.00(1H, t, J = 8.3Hz), 10.10(1H, s), 10.34(1H, s). 670 δ 2.28 (6H, s), 7.31-7.44 (5H, m), 7.57 (1H, t, J = 6.3Hz), 7.79 (1H, t, J = 7.3Hz), 8.07-8.09 (2H, m), 10.09 (1H, s), 10.32 (1H, s). 676 δ 7.34 (6H, s), 7.39 (1H, t, J =7.2Hz), 7.44 (2H, s), 7.59 (1H, t, J =7.2Hz), 7.83 (1H, t J =7.2Hz), 7.99 (2H, d, J =8.8Hz), 8.15 (2H, d, J =8.8Hz), 10.1 (1H, s), 10.57 (1H, s). 679 δ 2.35 (6H,s), 7.4 (1H, t, J =7.3Hz), 7.44 (2H, s), 7.61 (1H, t, J =7.3Hz), 7.84 (1H, t, J =7.3Hz), 8.24 (2H, d, J =8.8Hz), 8.41 (2H, d, J =8.8Hz), 10.11 (1H, s), 10.66 (1H, s). 682 δ 2.35 (6H, s), 7.38 (1H, t, J =8.1Hz), 7.44 (2H, s), 7.49 (1H, d, J =8.1Hz), 7.56 (1H, d, J =8.1Hz), 8.07 (2H, d, J =8.8Hz), 8.14 (2H, d, J =8.8Hz), 10.1 (1H, s), 10.43 (1H, s). 686 δ 234(6H, s), 7.23-7.28(2H, m), 7.38(1H, t, J = 7.8Hz), 7.44(2H, s), 7.52-7.65(2H, m), 8.05-8.10(1H, m), 10.12(1H, s), 10.88(1H, s). 699 δ 2.34 (6H, s), 3.39 (3H, s), 7.39 (1H, t, J =7.8Hz), 7.44 (2H, s), 7.49-7.59 (2H, m), 8.08-8.13 (2H, m), 8.55 (1H, dd, J =4.9,2.0Hz), 10.12 (1 H, s), 10.73 (1H, s). 708 (CDCl3) δ 7.39(1H, t, J = 7.8Hz), 7.48-7.64(3H, m), 7.88-7.96(4H, m), 8.09-8.13(2H, m), 8.69(1H, t, J = 7.8Hz), 8.75(1H, d, J = 7.8Hz). 711 (CDCl3) δ 7.22(1H, d, J = 8.3Hz), 7.35-7.40(2H, m), 7.56-7.62(1H, m), 7.91(1H, t, J = 7.3Hz), 7.96(2H, s), 8.15(1H, d, J = 13.3Hz), 8.22(1H, dt J = 1.9, 8.3Hz), 8.73 (1H, dt, J = 1.5. 8.3Hz), 8.92(1H, d, J = 17.1Hz). 719 (CDCl3) δ 7.41(1H, t, J = 8.3Hz), 7.85(2H, d, J = 8.3Hz), 7.92(1H, d, J = 6.9Hz), 7.96(2H, s), 8.03(2H, d, J = 8.3Hz), 8.06(1H, s), 8.10(1H, s), 8.63(1H, dt, J = 1.5, 8.3Hz). 722 (CDCl3) δ 7.42(1H, t, J = 8.3Hz), 7.93(1H, d, J = 5.3Hz), 7.96(2H, s), 8.06(1H, d, J = 12.2Hz), 8.10(2H, d, J = 8.8Hz), 8.13(1H, s), 8.40(2H, d, J = 8.8Hz), 8.64(1H, dt, J = 1.5. 8.3Hz). 791 (CDCl3) δ 2.34(6H, s), 7.37(1H, t, J=7.8Hz), 7.45(2H, s), 7.54(2H, t, J=7.8Hz), 7.61(1H, d, J=7.8Hz), 7.80(1H, d, J=11.7Hz), 7.82-7.87(1H, m), 7.92(2H, d, J=7.8Hz), 8.12(1H, s), 8.62 (1H, dt, J=20. 7.8Hz). 831 (CDCl3) δ 7.46-7.64(6H, m), 7.93-7.96(4H, m), 8.61(1H, s), 7.75(1H, dd, J = 1.9, 8.3Hz). 832 (CDCl3) δ 7.24(1H, d, J = 8.3Hz), 7.36(1H, t, J = 8.3Hz), 7.47(1H, t, J = 8.3Hz), 7.55-7.62(3H, m), 7.96(2H, s), 8.21(1H, dt J = 2.0, 8.3Hz), 8.77(1H, dd, J = 2.0, 8.3Hz), 9.33(1H, d, J = 16.6Hz). -
[Table 6-16] Compound No. 1H-NMR (DMSO-d6. ppm) 833 (CDCl3) δ 7.45-7.52(3H, m), 7.60(1H, d, J = 8.8Hz), 7.96(2H. s), 8.29(1H, d, J = 7.8Hz), 8.57(1H, dd, J = 20, 4.4Hz), 8.72(1H, d, J = 7.8Hz), 9.00(1H, s). 1001 δ 2.20 (6H, s), 3.45 (3H, s), 7.23-7.30 (5H, m), 7.43-7.45 (4H, m), 7.73-7.76 (2H, m), 9.88 (1H, s). 1013 δ 2.20(6H, s), 3.48(3H, s), 7.39-7.97(8H, m), 7.43(2H, s), 9.90(1H, s). 1016 δ 2.21 (6H, s), 3.46 (3H, s), 7.40-8.03 (10H, m), 9.91 (1H. s). 1032 δ 208(3H, s), 2.30(6H, s), 7.45(2H, s), 7.47(1H, d, J = 7.8Hz), 7.54(1H, t, J = 7.8Hz), 7.66(1H, d, J = 7.8Hz), 7.75(1H, d, J = 7.8Hz), 7.82(1H, d, J = 7.8Hz), 8.04(1H. dd, J = 2.0,7.8Hz), 8.13(1H, s), 8.35(1H, s), 9.99(1H, s), 10.16(1H, s), 10.48(1H, s). 1043 (CDCl3) δ 1.38(6H, m), 2.37(6H, s), 3.13(1H, broad), 3.33(3H, broad), 3.78(1H, broad), 3.89(1H, broad), 7.37(2H, s), 7.48(1H, d, J = 7.8Hz), 7.58(1H, t, J = 7.8Hz), 7.77(1H, s), 7.90(1H, s), 7.93(1H, broad). 1089 (CDCl3) δ 0.89(3H, t, J = 7.3Hz), 1.53-1.62(2H, m), 2.61 (2H, t, J = 7.3Hz), 3.50(3H, broad), 6.80(1H, broad), 7.03(1H, broad), 7.22(1H, broad), 7.34(3H, broad), 7.47(1H, s), 7.67-7.76 (3H, broad-m), 7.93(1H, s). 1091 (CDCl3) δ 0.88(3H, t, J = 7.3Hz), 1.53-1.63(2H, m), 2.62(2H, t, J = 7.8Hz), 3.52(3H, s), 6.83-6.89(2H, m), 7.26-7.32(3H, m), 7.41(1H, t, J = 7.8Hz), 7.48(1H, s), 7.66(1H, s), 7.76(2H, d, J = 8.8Hz), 7.93(1H, d, J = 1.5Hz). 1097 (CDCl3) δ 0.90(3H, t, J = 7.3Hz), 1.55-1.65(2H, m), 2.64(2H, t, J = 7.8Hz), 3.55(3H, s), 7.27(1H, s), 7.40-7.44(3H, m), 7.49-7.51(3H, m), 7.59(1H, s), 7.69(1H, s), 7.76(1H, d, J = 7.8Hz), 7.95(1H, s). 1100 (CDCl3) δ 0.88(3H, t, J = 7.3Hz), 1.54-1.64(2H, m), 2.63(2H, t, J = 7.8Hz), 3.56(3H, s), 7.29(1H, s), 7.40-7.50(4H, m), 7.59(1H, s), 7.71(1H, s), 7,76(1H, d, J = 7.3Hz), 7.94(1H, d, J = 1.5Hz), 8.06(2H, d, J = 8.8Hz). 1125 (CDCl3) δ 2.25(6H, s), 3.54(3H, s), 6.84(1H, broad-s), 7.00-7.10(2H, m), 7.20-7.40(6H, m), 7.50-7.60(1H, broad), 7.60-7.70(1H, broad). 1126 (CDCl3) δ 3.57(3H, s), 7.20-7.24(2H, m), 7.29-7.32(3H, m), 7.34(1H, t, J=7.8Hz), 7.40-7.44(2H, m), 7.57(1H, d, J=7.8Hz), 7.86-7.91(1H, m), 7.92(2H, s). 1206 δ 1.17 (3H, broad), 2.22 (6H, s), 3.94 (2H, broad), 7.01-7.08 (2H, m), 7.29-7.43 (6H, m), 7.72-7.77 (2H, m), 9.90 (1H, s). 1207 δ 1.26 (3H, t, J =6.8Hz), 2.04 (6H, s), 4.11 (2H, q, J =6.8Hz), 7.16-7.70 (12H, m). 1208 δ 2.28 (6H, s), 3.36 (3H, s), 7.27-7.32 (6H, m), 7.43 (2H, s), 7.55-7.57 (2H, broad), 9.96 (1H, s). 1209 δ 2.28 (6H, s), 3.47 (3H, s), 6.98 (1H, broad), 7.11 (2H, broad), 7.19 (1H, broad), 7.37 (1H. broad), 7.44 (2H, s), 7.51 (1H, broad), 7.74 (1H, broad), 9.94 (1H, s). 1210 δ 2.23 (3H, s), 2.29 (6H, s), 7.07-7.26 (5H, m), 7.44 (2H, s), 7.56-7.77 (2H, m), 9.98 (1H, s). 1211 δ 2.24 (3H, s), 2.28 (6H, s), 7.08-7.09 (2H, m), 7.22-7.28 (2H, m), 7.44 (2H, s), 7.51-7.58 (3H, m), 9.99 (1H, s). 1212 δ 2.29 (6H, s), 3.12 (3H, s), 7.17-8.02 (9H, m), 9.95 (1H, s). 1213 δ 2.26 (6H, s), 3.41 (3H, s), 7.12-8.34 (9H, m), 9.92 (1H, s). -
[Table 6-17] Compound No. 1H-NMR (DMSO-d6, ppm) 1214 δ 2.26 (6H, s), 3.40 (3H, s), 7.29 (1H, broad), 7.44 (2H, s), 7.59-7.81 (4H, m), 8.12 (2H, broad), 9.91 (1H, s). 1215 δ 2.26 (6H, s), 3.40 (3H, s), 7.31-7.39 (7H, m), 7.50-7.56 (1H, m), 7.81-7.83 (1H, m), 9.94 (1H, s). 1216 δ 2.27 (6H, s), 3.39 (3H, s), 7.31 (1H, m), 7.47 (2H, s), 7.60-7.67 (3H, m), 7.72-7.80 (3H, m), 9.96 (1 H, s). 1217 δ 2.27 (6H, s), 3.37 (3H, s), 7.29 (2H, broad), 7.44-7.48 (3H, m), 7.59-7.64 (2H, m), 7.76 (2H, broad), 9.94 (1H, s). 1218 δ 2.27 (6H, s), 3.39 (3H, s), 7.03-7.72 (9H, m), 9.94 (1H, s). 1219 δ 2.28 (6H, s), 3.36 (3H, s), 7.18-8.04 (9H, m), 9.98 (1H, m). 1220 δ 2.28 (6H, s), 3.34 (3H, s), 7.12-7.56 (9H, m), 9.97 (1H, s). 1229 δ 2.28 (6H, s), 3.39 (3H, s), 7.02-7.28 (2H, m), 7.35-7.43 (2H, m), 7.55-7.70 (2H, m), 7.93-7.99 (2H, m), 9.95 (1H, m). 1235 δ 2.26(6H, s), 3.43(3H, s), 7.27(1H, t, J = 7.8Hz), 7.44(2H, s), 7.58-7.65(2H, m), 7.71(1H, t, J = 7.8), 8.00(1H, dd, J = 8.3.2.0Hz), 8.04(1H, dd, J = 9.3,2.0Hz), 9.91(1H, s). 1236 δ 2.29 (6H, s), 3.41 (3H, s), 7.44-7.46 (3H, m), 7.59-7.61 (2H, m), 7.72-7.77 (1H, m), 7.88 (1H, d, J =6.8Hz), 7.95-7.99 (1H, m), 9.95 (1H, s). 1237 δ 2.29 (6H, s), 3.40 (3H, s), 7.08-7.91 (8H, m), 9.94 (1H, s). 1238 δ 2.28 (6H, s) 3.39 (3H, s), 7.21-7.28 (1H, m), 7.34-7.44 (3H, m), 7.54-7.60 (2H, m), 7.79-7.91 (2H, m), 9.95 (1 H, m). 1244 (CDCl3) δ 2.29(6H, s), 3.52(3H, s), 7.21-7.23(1H, m), 7.28-7.30(1H, m), 7.35(2H, m), 7.41(1H, m), 7.72(2H, m), 8.01(1H, t, J = 6.8Hz), 8.53(2H, m). 1245 δ 2.28 (6H, s), 3.41 (3H, s), 7.25 (1H, t, J =7.6Hz), 7.36 (1H, d, J =4.7Hz), 7.44 (2H, s), 7.57-7.64 (2H, m), 7.92 (1H, d, J =7.6Hz), 8.32 (1H, dd, J =4.7,1.9Hz), 9.97 (1H, s). 1246 δ 2.31 (6H, s), 3.60 (3H, s), 7.25-7.31 (2H, m), 7.44 (2H, s), 7.57-7.59 (2H, m), 7.97-8.01 (1H, m), 8.17-8.18 (1H, m), 9.97 (1H, s). 1247 δ 2.28 (6H, s), 3.39 (3H, s), 7.33 (1H, d, J =7.6Hz), 7.44 (2H, s), 7.61-7.69 (3H, m), 7.80 (1H, broad), 8.30 (1H, broad), 10.01(1H, s). 1255 δ 2.29 (6H, s), 3.35 (3H, s), 7.19-7.70 (10H, m), 9.98 (1H, s). 1256 δ 2.28 (6H, s), 2.30 (3H, s), 3.32 (3H, s), 6.98-7.72 (9H, m), 9.93 (1H, s). 1257 δ 2.23 (3H, s), 2.29 (6H, s), 3.34 (3H, s), 7.07-7.38 (5H, m), 7.53-7.76 (2H, m), 7.43 (2H, s), 9.98 (1H, s). 1258 δ 2.27 (6H, s), 2.33 (3H, s), 3.31 (3H, s), 6.98-7.51 (9H, s), 9.93 (1H, s). -
[Table 6-18] Compound No. 1H-NMR (DMSO-d6, ppm) 1259 δ 2.29 (6H, s), 3.41 (3H, s), 7.18 (1H, J = 7.3Hz), 7.44(2H, s), 7.46-7.57 (2H, m), 7.67 (1H, t, J =7.3Hz), 7.73-7.82 (2H, m), 8.01 (1H, d, J =7.8Hz), 9.95 (1H, s). 1260 δ 2.26 (6H, s), 3.36 (3H, s), 7.42 (2H, s), 7.59 (1H, broad), 7.7 (1H, broad), 7.82 (1H, t, J =7.9Hz), 8.2 (1H, broad), 8.34-8.37 (1H, m), 8.48 (1H, dd, J =7.9,1.7Hz), 8.62 (1H, t, J =2.0Hz), 9.92 (1H, s). 1261 δ 2.27 (6H, s), 3.37 (3H, s), 7.43 (2H, s), 7.59-7.65 (2H, m), 8.11 (1H, broad), 8.18 (2H, d, J =8.8Hz), 8.29 (2H, d, J =8.8Hz), 9.91 (1H, s). 1262 δ 2.33 (6H, s), 3.35 (3H, s), 7.30-7.83 (9H, m), 9.93 (1H, s). 1263 δ 2.27 (6H, s), 3.37 (3H, s), 7.18-7.80 (9H, m), 9.96 (1H, s). 1264 δ 2.27 (6H, s), 3.35 (3H, s), 7.43 (2H, s), 7.48 (1H, broad), 7.58 (1H, broad), 7.75 (1H, broad), 7.99 (2H, d, J =8.5Hz), 8.08 (2H, d, J =8.5Hz), 9.95 (1H, s). 1265 δ 2.27 (6H, s), 3.36 (3H, s), 7.03-7.73 (9H, m), 9.93 (1H, s). 1266 δ 2.28 (6H, s), 3.35 (2H, s), 7.18-7.61 (9H, m), 9.99 (1H, s). 1267 δ 2.28 (6H, s), 3.39 (3H, s), 7.11-7.18 (3H, m), 7.26-7.30 (1H, t, J =7.8Hz), 7.40-7.47 (3H, m), 7.58 (2H, t, J =7.6Hz), 9.96 (1H, s). 1274 δ 2.27 (6H, s), 3.37 (3H, s), 7.29 (3H, broad), 7.41-7.47 (4H, m), 7.59-7.61 (2H, m), 9.95 (1H, s). 1293 δ 2.28 (6H, s), 3.41 (3H, s), 7.25 (1H, t, J =7.6Hz), 7.35 (1H, dd, J =7.3,4.9Hz), 7.43 (2H, s), 7.57-7.63 (2H, m), 7.91 (1H, d. J =7.6Hz), 8.32 (1H, dd, J =4.9,2.0Hz), 9.96 (1H, s). 1294 δ 2.28 (6H, s), 3.39 (3H, s), 7.31-7.35 (1H, m), 7.42 (2H, s), 7.43-7.48 (1H, m), 7.61-7.75 (2H, m), 7.80 (1H, s), 8.32 (1H, broad), 10.01 (1H, s). 1463 δ 2.25(6H, s), 3.38(3H, s), 7.27-7.41(6H, m). 7.45(2H, s), 7.90(1H, broad), 8.05(1H, d, J = 6.8Hz), 9.96(1H, s). 1464 δ 223(6H, s), 3.42(3H, s), 7.41(1H, broad), 7.45(2H, s), 7.60(2H, broad), 7.90(1H, broad), 8.08-8.13(3H, broad), 9.93(1H, s). 1465 δ 225(6H, s), 3.40(3H, s), 7.39-7.42(1H, m), 7.45(2H, s), 7.50(1H, broad), 7.78(1H, broad), 7.91(1H, broad), 7.97-8.10(3H, m), 9.94(1H, s). 1478 δ 229(6H, s), 3.24(3H, s), 6.84(1H, d, J = 7.8Hz), 7.12(1H, t, J = 7.8Hz), 7.33(2H, s). 7.50-7.64(4H, m), 7.85-7.88(2H, m), 7.98-8.03(1H, m), 10.22(1H, s). 1479 δ 2.41(3H, s), 3.25(3H, s), 6.95(1H, dd, J = 1.5,7.8Hz), 7.16(1H, t, J = 7.8Hz), 7.50-7.64(4H, m), 7.68(1H, s), 7.86-7.88(2H, m), 7.93(1H, t, J = 1.5Hz), 7.98-8.00(1H, m), 10.24(1H, s). 1480 (CDCl3) δ 3.34(3H, s), 7.13-7.19(2H, m), 7.49-7.58(3H, m), 7.70-7.73(2H, m), 7.78-7.91(4H, m), 8.12(1H, s). 1481 (CDCl3) δ 3.35(3H, s), 7.15-7.20(3H, m), 7.32(1H, t, J = 7.8Hz), 7.51-7.55(1H, m), 7.71(1H, d, J = 2.9Hz), 7.72(1H, d, J = 2.0Hz), 7.80(2H, s), 8.14(1H, dt, J = 2.0, 7.8Hz), 8.37(1H, d, J = 16.1Hz). 1482 δ 1.18(3H, t, J = 7.3Hz), 2.30(6H, s), 3.76(2H, q, J = 7.3Hz), 6.81(1H, d, J = 7.8Hz), 7.11(1H, t, J = 7.8Hz), 7.33(2H, s), 7.50-7.62(4H, m), 7.84-7.88(2H, m), 7.95-8.00 (1H, m). 10.20(1H, s). -
[Table 6-19] Compound No. 1H-NMR(DMSO-d6, ppm) 1483 δ 1.44(6H, d, J = 6.3Hz), 2.07(6H, s), 5.35(1H, septet, J = 6.3Hz), 6.84(1H, d, J = 7.8Hz), 7.21(1H, t, J = 7.8Hz), 7.21(2H, s), 7.50-7.61(3H, m), 7.75(1H, dd, J = 1.5, 7.8Hz), 7.86-7.89(3H, m), 10.29(1H, s). 1484 δ 2.18 (3H, s), 2.32 (6H, s), 7.37-7.59 (11H, m), 10.42 (1H, s). 1485 δ 2.34 (3H, s), 2.35 (6H, s), 7.34-8.02 (10H, m), 10.33 (1H, s). 1486 δ 2.33 (3H, s), 2.36 (6H, s), 7.29-8.12 (9H, m), 10.37 (1H, s). 1487 δ 2.20 (6H, s), 3.08 (3H, s), 3.20 (3H, s), 6.93-7.39 (10H, m), 7.45-7.51 (1H, m). 1607 (CDCl3) δ 3.31(3H, s), 3.35(3H, s), 6.81(1H, dt, J = 6.8, 1.0Hz), 6.94(1H, t, J = 7.8Hz), 7.10-7.24(5H, m), 7.35-7.40(1H, m), 7.41(1H, s), 7.78(2H, s). 1617 (CDCl3) δ 3.30(3H, s), 3.33(3H, s), 6.76-7.00(4H, m), 7.19-7.23(3H, m), 7.37(1H, s), 7.77(2H, s). 1645 (CDCl3) δ 3.30(3H, s), 3.36(3H, s), 6.96-7.06(3H, m), 7.12-7.16(1H, m), 7.39-7.42(2H, m), 7.95(2H, s), 8.24(1H, s). 1654 (CDCl3) δ 3.30(3H, s), 3.42(3H, s), 7.01(1H, d, J = 7.3Hz), 7.10(1H, t, J = 7.8Hz), 7.16(1H, dd, J = 1.4, 7.8Hz), 7.41(1H, t, J = 1.4Hz), 7.54(1H, dd, J = 1.9Hz), 7.56(1H, d, J = 1.9Hz), 7.80(1H, s), 7.81(2H, s). 1655 (CDCl3) δ 3.29(3H, s), 3.38(3H, s), 3.78(3H, s), 6.73(1H, d, J = 8.3Hz), 6.96(1H, d, J = 8.3Hz), 7.04(1H, t, J = 7.8Hz), 7.08(1H, d, J = 1.5Hz), 7.14(1H, d, J = 7.8Hz), 7.40(1H, s), 7.54(1H, d, J = 8.3Hz), 7.81(2H, s). 1697 δ 2.23 (6H, s), 3.32 (3H, s), 3.39 (3H, s), 7.15-7.43 (10H, m). 2001 (CDCl3) δ 2.36 (6H, s), 7.36 (2H, s), 7.53-7.57 (2H, m), 7.61-7.65 (1H, m), 7.95-8.03 (3H, m), 8.08 (1H, dd, J =7.3,1.0Hz), 8.52 (1H, broad-s), 8.62 (1H, dd, J =8.3,1.0Hz), 9.19 (1H, broad-s). 2004 δ 2.30 (6H, s), 7.37-7.43 (2H, m), 7.46 (2H, s), 7.65 (1H, d, J =8.1Hz), 7.83 (1H, dd, J =7.5,5.6Hz), 7.88 (1H, d, J =7.5Hz), 8.13 (1H, t, J =8.1Hz), 8.40 (1H, d, J =8.1Hz), 10.08 (1H, s), 10.62 (1H, s). 2032 δ 2.30 (6H, s), 7.46 (2H, s), 7.75-7.78 (1H, m), 7.91 (1H, dd, J =7.3,1.0Hz), 8.13-8.18 (2H, m), 8.27 (1H, d, J =8.0Hz), 8.56 (1H, d, J =8.0Hz), 8.77 (1H, d, J =1.0Hz), 10.62 (1H, s), 10.75 (1H, s). 2033 δ 2.27(6H, s), 6.16(2H, s), 6.71(1H, d, J = 7.6Hz), 7.01(2H, d, J = 1.0Hz), 7.24(1H, d, J = 6.9Hz), 7.42(2H, s), 7.59(1H, dd, J = 7.6,6.9Hz), 7.65(1H, s), 9.94(1H, s). 2034 δ 2.32 (6H, s), 7.47 (2H, s), 7.90-7.93 (3H, m), 8.15 (1H, t, J =8.0Hz), 8.37 (1H, d, J =8.0Hz), 8.83 (2H, dd, J =4.6,1.7Hz), 10.12 (1H, s), 10.92 (1H, s). 2035 δ2.30 (6H, s), 7.46 (2H, s), 7.55-7.56 (1H, m), 7.89 (1H, d, J =7.4Hz), 8.14 (1H, t, J =7.8Hz), 8.34-8.41 (2H, m), 8.45 (1H, dd, J =5.4,1.2Hz), 10.03 (1H, s), 10.90 (1H, s). 2036 δ2.29 (6H, s), 7.45 (2H, s), 7.59 (1H, t. J =6.3Hz), 7.88 (1 H, d, J =6.3Hz), 8.12-8.16 (2H, m), 8.39 (1H, m), 8.55 (1H, m), 9.93 (1H, s), 11.25 (1H, s). 2037 δ2.32 (6H, s), 7.47 (2H, s), 7.67 (1H, d, J =7.6Hz), 7.75 (1H, d, J =8.3Hz), 7.90 (1H, d. J =7.6Hz), 8.14 (1H, t, J =7.6Hz), 8.29 (1H, dd, J =8.3Hz, 2.0Hz), 8.89 (1H, d, J =2.0Hz), 10.07 (1H, s), 10.97 (1H, s). 2082 δ2.20 (6H, s), 3.58 (3H, s), 7.29-7.39 (5H, m), 7.43 (2H, s), 7.50 (1H, d, J =7.4Hz), 7.83 (1H, t, J =7.4Hz), 7.94 (1H, t, J =7.4Hz), 9.91 (1H, s). -
[Table 6-20] compound No. 1H-NMR (DMSO-d6, ppm) 2085 δ2.22 (6H, s), 3.57 (3H, s), 7.12 (1H, t, J =9.2Hz), 7.20 (1H, t, J =7.3Hz), 7.28-7.30 (1H, m), 7.44 (2H, s), 7.55 (1 H, t, J =7.2Hz), 7.63 (1 H, broad), 7.87 (1 H, d, J =7.2Hz), 7.98 (1H, t, J =7.2Hz), 9.90 (1 H, s). 2093 δ 2.14(6H, s), 3.57(3H, s), 7.42(2H, s), 7.66-7.87(3H, m), 7.96-8.09(4H, m), 9.77(1H, s). 2116 δ 2.23 (6H, s), 3.55 (3H, s), 7.45 (3H, s), 7.89-9.91 (2H, m), 8.03-8.10 (3H, m), 9.82 (1H, s). 2117 δ 2.13 (6H, s), 3.58 (3H, s), 7.42 (2H, s), 7.46 (1H, d, J =8.2Hz), 7.72-7.75 (2H, m), 7.90 (1 H, d, J =8.2Hz), 8.08 (1H, t, J =8.2Hz), 8.35 (1 H, d, J =2.0Hz), 9.83 (1H, s). 2162 (CDCl3) δ 2.38 (6H, s), 7.38 (2H, s), 7.53-7.57 (2H, m), 7.62 (1H, d, J =7.8Hz), 7.68 (1H, dd, J =4.9,1.5Hz), 7.85 (1H, broad-s), 7.95 (2H, d, J =7.8Hz), 8.52 (1H, d, J =4.9Hz), 8.22 (1H, broad-s), 8.88 (1H, s). 2163 (CDCl3) δ 2.36 (6H, s), 7.38 (2H, s), 7.55-7.59 (2H, m), 7.64-7.72 (2H, m), 7.75 (1H, broad-s), 8.01 (2H, d, J =7.3Hz), 8.41 (1 H, d, J =6.8Hz), 9.14 (1H, d, J =2.4Hz), 10.9 (1 H, broad-s). 2164 (CDCl3) δ 2.34 (6H, s), 7.47 (2H, s), 7.62-7.65 (2H, m), 7.70-7.81 (2H, m), 8.04-8.04 (3H, m), 8.64 (1H, dd, J =8.3,1.5Hz), 10.9 (1H, broad-s), 12.3 (1H, broad-s). 2165 δ 2.35 (6H, s), 7.29-8.03 (10H, m), 8.75 (1H, d, J =2.0Hz). 2168 δ 2.25 (6H, s), 3.32 (3H, s), 7.26 (1H, d, J =7.7Hz), 7.38 (1H, d, J =7.7Hz), 7.44 (2H, s), 7.55 (1H, t, J =7.7Hz), 7.90 (3H, m), 8.11 (2H, m), 12.40 (1H, s). 2201 (CDCl3) δ 2.38(6H,s),7.25-8.00(11H,m),8.34(1H,s),8.85(1H,broad.). 2202 (COCl3) δ 2.36 (6H, s), 7.37 (2H, s), 7.47-7.61(5H,m), 7.85-8.03 (4H,m), 8.57 (1 H,s),9.18(1H,s). 2203 (COCl3) δ 2.38 (6H,s), 7.41 (2H, s), 7.45-7.55 (4H, m), 7.90-7.96 (4H,m) ,8.57 (1H, broad),8.74 (1H,broad), 9.18(1H,broad). - Typical compounds of the compound represented by the general formula (2) that is an active ingredient of the insecticide of the present invention are illustrated in Table 7 below, but the present invention is not restricted thereto.
-
- Typical compounds of the compound represented by the general formula (3) that is an active ingredient of the fungicide of the present invention are illustrated in Table 8 below, but the present invention is not restricted thereto.
- Incidentally, in Table 8, Me refers to a methyl group, i-Pr refers to an isopropyl group, and t-Bu refers to a tertiary butyl group.
-
- Typical compounds of the compound represented by the general formula (4) that is an active ingredient of the fungicide of the present invention are illustrated in Table 9 below, but the present invention is not restricted thereto.
- Incidentally, in Table 9, Me refers to a methyl group, i-Pr refers to an isopropyl group, and t-Bu refers to a tertiary butyl group.
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- The insecticidal and fungicidal composition of the present invention exhibits excellent insecticidal and fungicidal effects and exerts an accurate control effect on harmful diseases and insect pests. As such insect pests, there can be exemplified, for example, LEPIDOPTERA such as swift moth (Endoclyta excrescens), grape tree-borer (Endoclyta sinensis), swift moth (Palpifer sexnotata), strawberry tortrix moth (Acleris comariana), summer fruit tortrix moth (Adoxophyes orana fasciata), small tea tortrix moth (Adoxophyes sp.), Asiatic leaf roller (Archips breviplicanus), apple tortrix (Archips fuscocupreanus), brown oak tortrix (Archips xylosteanus), tortrix moth (Bactra furfurana), tobacco leaf worm (Cnephasia cinereipalpana), nut fruit tortrix (Cydia kurokoi), greenish chestnut moth (Eucoenogenes aestuosa), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), oriental tea tortrix moth (Homona magnanima), leaf roller (Hoshinoa adumbratana), soybean pod borer (Leguminivora glycinivorella), adzuki bean pod worm (Matsumuraeses azukivora), soybean pod worm (Matsumuraeses falcana), soybean pod worm (Matsumuraeses phaseoli), mulberry leaf roller (Olethreutes mori), apple fruit licker (Spilonota lechriaspis), eye-spotted bud moth (Spilonota ocellana), European grape berry moth (Eupoecillia ambiguella), arrowhead moth (Phalonidia mesotypa), mugwort moth (Phtheochroides clandestine), codling moth (Cydia pomonella), grape berry moth (Endopiza viteana), mulberry bagworm (Bambalina sp.), giant bagworm (Eumeta japonica), tea bagworm (Eumeta minuscula), European grain moth (Nemapogon granellus), case making clothes moth (Tinea translucens), pear leaf miner (Bucculatrix pyrivorella), peach leaf miner (Lyonetia clerkella), apple leaf miner (Lyonetia prunifoliella), soybean leaf roller (Caloptilia soyella), tea leaf roller (Caloptilia theivora), apple leaf miner (Caloptilia zachrysa), persimmon leaf miner (Cuphodes diospyrosella), apple leaf miner (Phyllonorycter ringoniella), pear bark miner (Spulerina astaurota), citrus leaf miner (Phyllocnistis citrella), grape leaf miner (Phyllocnistis toparcha), allium leaf miner (Acrolepiopsis sapporensis), yam leaf miner (Acrolepiopsis suzukiella), diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), grape clearwing moth (Paranthrene regalis), cherry tree borer (Synanthedon hector), persimmon fruit moth (Stathmopoda masinissa), sweet potato leaf folder (Brachmia triannulella), pink bollworm (Pectinophora gossypiella), potato tuber moth (Phthorimaea operculella), peach fruit moth (Carposina niponensis), pear leaf worm (Illiberis pruni), Chinese cochlid (Latoia sinica), oriental moth (Monema flavescens), pear stinging caterpillar (Narosoideus flavidorsalis), green stinging caterpillar (Parasa consocia), persimmon cochlid (Scopelodes contracus), rice striped stem borer (Chilo suppressalis), rice leaffolder (Cnaphalocrocis medinalis), yellow peach moth (Conogethes punctiferalis), cucumber moth (Diaphania indica), pear fruit moth (Ectomyelois pyrivorella), tobacco moth (Ephestia elutella), Mediterranean flour moth (Ephestia kuehniella), limabean pod borer (Etiella zinckenella), persimmon bark borer (Euzophera batangensis), mulberry pyralid (Glyphodes pyloalis), cabbage webworm (Hellulla undalis), rice leaf roller (Marasmia exigua), legume pod borer (Maruca testulalis), cotton leaf roller (Notarcha derogate), Asian corn borer (Ostrinia furnacalis), adzuki bean borer (Ostrinia scapulalis), butterbur borer (Ostrinia zaguliaevi), bluegrass webworm moth (Parapediasia teterrella), peppered moth (Pleuroptya ruralis), Indian-meal moth (Plodia interpunctella), yellow stem borer (Scirpophaga incertulas), common straight swift butterfly (Parnara guttata), large swallowtail butterfly (Papilio helenus), papilionid butterfly (Papilio machaon hippocrates), citrus swallowtail butterfly (Papilio xuthus), Eastern pale clouded yellow (Colias erate poliographus), small white butterfly (Pieris rapae crucivora), long-tailed pea-blue (Lampides boeticus), orange moth (Angerona prunaria), Japanese giant looper (Ascotis selenaria), giant geometrid moth (Biston robustum), plum cankerworm (Cystidia couaggaria), pine moth (Dendrolimus spectabilis), tent moth (Malacosoma neustria testacea), apple caterpillar (Odonestis pruni japonensis), coffee hawk moth (Cephonodes hylas), hawk moth (Acosmeryx castanea), scarce chocolate-tip (Clostera anachoreta), poplar tip moth (Clostera anastomosis), black-marked prominent (Phalera flavescens), drab-brown moth (Phalerodonta manleyi), lobster moth (Stauropus fagi persimilis), tea tussock moth (Euproctis pseudoconspersa), brown tail moth (Euproctis similis), oriental tussock moth (Euproctis subflava), Asian gypsy moth (Lymantria dispar), white-spotted tussock moth (Orgyia thyellina), fall webworm moth (Hyphantria cunea), mulberry tiger moth (Spilosoma imparilis), three-spotted plusia (Acanthoplusia agnata), sweet potato leaf worm (Aedia leucomelas), black cutworm (Agrotis ipsilon), turnip moth (Agrotis segetum), cotton looper (Anomis flava), hibiscus leaf caterpillar (Anomis mesogona), beet semi-looper (Autographa nigrisigna), tiger moth (Trichoplusia ni), American boll worm (Helicoverpa armigera), oriental tobacco budworm (Helicoverpa assulta), flax budworm (Heliothis maritima), cabbage moth (Mamestra brassicae), green rice semilooper (Naranga aenescens), growth-blocking peptide (Pseudaletia separata), pink stem borer (Sesamia inferens), Japanese lawn grass cutworm (Spodoptera depravata), beet armyworm (Spodoptera exigua), oriental leafworm moth (Spodoptera litura), apple dagger moth (Triaena intermedia), sorrel cutworm (Viminia rumicis), spotted cutworm moth (Xestia c-nigrum) and the like;
Heteroptera of HEMIPTERA such as globular stink bug (Megacopta punctatissimum), black-shouldered shield bug (Carpocoris purpureipennis), sloe bug (Dolycoris baccarum), cabbage bug (Eurydema pulchrum), cabbage bug (Eurydema rugosum), 2-spotted sesame bug (Eysarcoris guttiger), white-spotted larger spined bug (Eysarcoris lewisi), white-spotted bug (Eysarcoris parvus), white-spotted stink bug (Eysarcoris ventralis), fruit-piercing stink bug (Glaucias subpunctatus), red-striped stink bug (Graphosoma rubrolineatum), brown marmorated stink bug (Halyomorpha mista), rice stink bug (Lagynotomus elongatus), eastern green stink bug (Nezara antennata), southern green stink bug (Nezara viridula), redbanded shield bug (Piezodorus hybneri), brownwinged green bug (Plautia stali), black rice bug (Scotinophara lurida), shield bug (Starioides iwasakii), winter cherry bug (Acanthocoris sordidus), Coreid bug (Anacanthocoris striicornis), narrow squash bug (Cletus punctiger), slender rice bug (Cletus trigonus), leaf-footed bug (Molipteryx fulginosa), paddy bug (Leptocorisa acuta), rice bug (Leptocorisa chinensis), rice bug (Leptocorisa oratorius), bean bug (Riptortus clavatus), carrot bug (Aeschynteles maculatus), plant bug (Liorhyssus hyalinus), oriental chinch bug (Cavelerius saccharivorus), chinch bug (Macropes obnubilus), ground bug (Pachybrachius luridus), lygaeid bug (Paromius exguus), seed bug (Togo hemipterus), red cotton bug (Dysdercus cingulatus), red bug (Dysdercus poecilus), chrysanthemum lace bug (Galeatus spinifrons), lace bug (Metasalis populi), silver magnolia lace bug (Stephanitis fasciicarina), pear lace bug (Stephanitis nashi), azalea lace bug (Stephanitis pyrioides), chestnut lace bug (Uhlerites debile), walnut lace bug (Uhlerites latius), alfalfa plant bug (Adelphocoris lineolatus), plant bug (Adelphocoris triannulatus), green leaf bug (Apolygus lucorum), pale green plant bug (Apolygus spinolai), sweet potato yellow bug (Creontiades pallidifer), tobacco leaf bug (Cyrtopeltis tennuis), plant bug (Ectometopterus micantulus), plant bug (Halticiellus insularis), apple leaf bug (Heterocordylus flavipes), mirid bug (Lygus disponsi), lygus bug (Lygus saundersi), mirid bug (Orthotylus flavosparsus), plant bug (Stenodema calcaratum), mired plant bug (Stenotus binotatus), sorghum plant bug (Stenotus rubrovittatus), broken back bug (Taylorilygus pallidulus), rice leaf bug (Trigonotylus coelestialium) and the like;
Homoptera such as large brown cicada (Graptopsaltria nigrofuscata), spittle bug (Aphrophora costalis), pine spittle bug (Aphrophora flavipes), grape spittle bug (Aphrophora vitis), spittle bug (Clovia punctata), meadow spittle bug (Philaenus spumarius), black-tipped leafhopper (Bothrogonia japonica), green leafhopper (Cicadella viridis), white leafhopper (Cofana spectra), oak leafhopper (Aguriahana quercus), polyphagous leafhopper (Alnetoidia alneti), citrus leafhopper (Apheliona ferruginea), grape leafhopper (Arboridia apicalis), small green leafhopper (Edwardsiana flavescens), rose leafhopper (Edwardsiana rosae), spruce leafhopper (Empoasca abietis), tea green leafhopper (Empoasca onukii), yellow rice leafhopper (Thaia subrufa), small citrus leafhopper (Zyginella citri), aster leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cincticeps), green rice leafhopper (Nephotettix nigropictus), green leafhopper (Nephotettix virescens), apple leafhopper (Orientus ishidai), zigzag leafhopper (Recilia dorsalis), wheat leafhopper (Sorhoanus tritici), leafhopper (Speusotettix subfusculus), small brown plant hopper (Laodelphax striatellus), brown plant hopper (Nilaparvata lugens), planthopper (Numata muiri), maize planthopper (Peregrinus maidis), sugarcane planthopper (Perkinsiella saccharicida), white backed planthopper (Sogatella furcifera), panicum planthopper (Sogatella panicicola), mulberry psyllid (Anomoneura mori), psyllid (Calophya nigridorsalis), Asian citrus psyllid (Diaphorina citri), psyllid (Mesohomotoma camphorae), abies sucker (Psylla abieti), jumping plant louse (Psylla alni), Japanese louse (Psylla jamatonica), apple psyllid (Psylla mali), black apple sucker (Psylla malivorella), larger pear sucker (Psylla pyrisuga), Tobira sucker (Psylla tobirae), camphor sucker (Trioza camphorae), sucker (Trioza quercicola), spiny whitefly (Aleurocanthus spiniferus), grape whitefly (Aleurolobus taonabae), sweet potato whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), greenhouse whitefly (Trialeurodes vaporariorum), silver leaf whitefly (Bemisia argentifolii), grape phylloxera (Viteus vitifolii), root aphid (Aphidounguis mali), woolly apple aphid (Eriosoma lanigerum), sugarcane root aphid (Geoica lucifuga), pea aphid (Acyrthosiphon pisum), spiraea aphid (Aphis citricola), cowpea aphid (Aphis craccivora), willow aphid (Aphis farinose yanagicola), cotton-melon aphid (Aphis gossypii), foxglove aphid (Aulacorthum solani), leafcurl plum aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), tulip bulb aphid (Dysaphis tulipae), European birch aphid (Euceraphis punctipennis), mealy plum aphid (Hyalopterus pruni), mustard aphid (Lipaphis erysimi), chrysanthemum aphid (Macrosiphoniella sanborni), potato aphid (Macrosiphum euphorbiae), bean aphid (Megoura crassicauda), pear aphid (Melanaphis siphonella), apple leaf-curling aphid (Myzus malisuctus), plum aphid (Myzus mumecola), green peach aphid (Myzus persicae), onion aphid (Neotoxoptera formosana), apple aphid (Ovatus malicolens), waterlily aphid (Rhopalosiphum nymphaeae), wheat aphid (Rhopalosiphum padi), rice root aphid (Rhopalosiphum rufiabdominalis), wormwood root aphid (Sappaphis piri), pear aphid (Schizaphis piricola), corn leaf aphid (Sitobion akebiae), rose aphid (Sitobion ibarae), black citrus aphid (Toxoptera aurantii), black citrus aphid (Toxoptera citricidus), peach aphid (Tuberocephalus momonis), Formosan lettuce aphid (Uroleucon formosanum), greenbug aphid (Schizaphis graminum), giant mealybug (Drosicha corpulenta), cottony cushion scale (Icerya purchasi), Matsumoto mealybug (Crisicoccus matsumotoi), pine mealybug (Crisicoccus pini), pear mealybug (Dysmicoccus wistariae), citrus mealybug (Planococcus citri), Japanese mealybug (Planococcus kraunhiae), citrus mealybug (Pseudococcus citriculus), comstock mealybug (Pseudococcus comstocki), Indian white wax scale (Ceroplastes ceriferus), pink wax scale (Ceroplastes rubens), soft scale (Coccus discrepans), brown soft scale (Coccus hesperidum), citricola scale (Coccus pseudomagnoliarum), Chinese white-wax scale (Ericerus pela), European fruit scale (Lecanium corni), European peach scale (Lecanium persicae), citrus cottony scale (Pulvinaria aurantii), cottony citrus scale (Pulvinaria citricola), cottony mulberry scale (Pulvinaria kuwacola), black scale (Saissetia oleae), citrus scale (Andaspis kashicola), California red scale (Aonidiella aurantii), citrus yellow scale (Aonidiella citrina), coconut scale (Aspidiotus destructor), oleander scale (Aspidiotus hederae), Florida red scale (Chrysomphalus ficus), San Jose scale (Comstockaspis perniciosa), dupla scale (Duplaspidiotus claviger), purple scale (Lepidosaphes beckii), oystershell scale (Lepidosaphes ulmi), pear scale (Lepholeucaspis japonica), pear scale (Parlatoreopsis pyri), armored scale (Parlatoria camelliae), tea black scale (Parlatoria theae), black parlatoria scale (Parlatoria ziziphi), fern scale (Pinnaspis aspidistrae), camphor scale (Pseudaonidia duplex), Japanese camellia scale (Pseudaonidia paeoniae), white peach scale (Pseudaulacaspis pentagona), white prunicola Scale (Pseudaulacaspis prunicola), arrowhead scale (Unaspis yanonensis) and the like;
COLEOPTERA such as brown chafer (Adoretus tenuimaculatus), cupreous chafer (Anomala cuprea), soybean beetle (Anomala rufocuprea), flower chafer (Eucetonia pilifera), flower beetle (Eucetonia roelofsi), yellowish elongate chafer (Heptophylla picea), cockchafer (Melolontha japonica), Japanese cockchafer (Mimela splendens), smaller green flower chafer (Oxycetonia jucunda), Japanese beetle (Popillia japonica), variegated carpet beetle (Anthrenus verbasci), black carpet beetle (Attagenus unicolor japonicus), cigarette beetle (Lasioderma serricorne), powder post beetle (Lyctus brunneus), corn sap beetle (Carpophilus dimidiatus), dried fruit beetle (Carpophilus hemipterus), herbivorous ladybird beetle (Epilachna vigintioctomaculata), spotted ladybird beetle (Epilachna vigintioctopunctata), Mexican bean beetle (Epilachna varivestis), black fungus beetle (Alphitobius laevigatus), beetle (Neatus picipes), flour beetle (Palorus ratzeburgii), depressed flour beetle (Palorus subdepressus), yellow mealworm beetle (Tenebrio molitor), rust red flour beetle (Tribolium castaneum), red flour beetle (Tribolium confusum), Japanese blister beetle (Epicauta gorhami), long-horn beetle (Aeolesthes chrysothrix), white-spotted longicorn beetle (Anoplophora malasiaca), Japanese pine sawyer beetle (Monochamus alternatus), yellow-spotted longicorn beetle (Psacothea hilaris), grape borer (Xylotrechus pyrrhoderus), monkeypod roundheaded borer (Xystrocera globosa), bean weevil (Acanthoscelides obtectus), Chinese bean weevil (Callosobruchus chinensis), southern cowpea weevil (Callosobruchus maculatus), cucurbit leaf beetle (Aulacophora femoralis), leaf beetle (Basilepta balyi), tortoise beetle (Cassida nebulosa), brown-blackish beetle (Chaetocnema concinna), chrysomelid leaf beetle (Colasposoma dauricum), asparagus leaf beetle (Crioceris quatuordecimpunctata), rice rootworm (Donacia provosti), alder chrysomelid beetle (Linaeidea aenea), leaf beetle (Luperomorpha tunebrosa), two-striped leaf beetle (Medythia nigrobilineata), rice leaf beetle (Oulema oryzae), tropical legume leaf beetle (Pagria signata), daikon leaf beetle (Phaedon brassicae), crucifer flea beetle (Phyllotreta striolata), Colorado potato beetle (Leptinotarsa decemlineata), corn root worm (Diabrotica sp.), weevil (Involvulus cupreus), peach curculio (Rhynchites heros), sweet potato weevil (Cylas formicarius), apple blossom weevil (Anthonomus pomorum), weevil (Ceuthorhynchidius albosuturalis), chestnut weevil (Curculio sikkimensis), rice-plant weevil (Echinocnemus squameus), West Indian sweet potato weevil (Euscepes postfasciatus), lesser clover leaf weevil (Hypera nigrirostris), Alfalfa weevil (Hypera postica), rice water weevil (Lissorhoptrus oryzophilus), Australian tomato weevil (Listroderes costirostris), common leaf weevil (Phyllobius armatus), Japanese weevil (Sitona japonicus), boll weevil (Anthonomus grandis), rice weevil (Sitophilus oryzae), maize weevil (Sitophilus zeamais), hunting billbug (Sphenophrus venatus vestitus), pine shoot beetle (Tomicus piniperda) and the like;
THYSANOPTERA such as grass thrips (Anaphothrips obscurus), cocksfoot thrips (Chirothrips manicatus), black tea thrips (Dendrothrips minowai), flower thrips (Frankliniella intonsa), thrips (Frankliniella lilivora), greenhouse thrips (Heliothrips haemorrhoidalis), composite thrips (Microcephalothrips abdominalis), oriental soybean thrips (Mycterothrips glycines), mulberry thrips (Pseudodendrothrips mori), yellow tea thrips (Scirtothrips dorsalis), redbanded thrips (Selenothrips rubrocinctus), oriental rice thrips (Stenchaetothrips biformis), thrips (Thrips alliorum), loquat thrips (Thrips coloratus), Eurasian yellow flower thrips (Thrips flavus), banana flower thrips (Thrips hawaiiensis), chrysanthemum thrips (Thrips nigropilosus), melon thrips (Thrips palmi), western flower thrips (Frankliniella occidentalis), light brown soybean thrips (Thrips setosus), gladiolus thrips (Thrips simplex), onion thrips (Thrips tabaci), rye thrips (Haplothrips aculeatus), Chinese thrips (Haplothrips chinensis), predatory thrips (Haplothrips kurdjumovi), red clover thrips (Haplothrips niger), thrips (Leeuwenia pasanii), camphor thrips (Liothrips floridensis), lily thrips (Liothrips vaneeckei), thrips (Litotetothrips pasaniae), Japanese gall-forming thrips (Ponticulothrips diospyrosi) and the like;
ORTHOPTERA such as American cockroach (Periplaneta americana), smokybrown cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta japonica), German cockroach (Blattella germanica), wild cockroach (Blattella lituricollis), Northern cone-headed long horn grasshopper (Homorocoryphus jezoensis), walker (Homorocoryphus lineosus), mole cricket (Gryllotalpa sp.), small rice grasshopper (Oxya hyla intricata), rice grasshopper (Oxya yezoensis), migratory locust (Locusta migratoria) and the like;
DIPTERA such as rice crane fly (Tipula aino), fungus gnat (Bradysia agrestis) , soybean pod gall midge (Asphondylia sp.), melon fly (Dacus cucurbitae) , oriental fruit fly (Dacus dorsalis) , Japanese orange fly (Dacus tsuneonis), Japanese cherry fruit fly (Rhacochlaena japonica), rice leaf miner (Hydrellia griseola), rice whorl maggot (Hydrellia sasakii), fruit fly (Drosophila suzukii), rice stem maggot (Chlorops oryzae), wheat stem maggot (Meromyza nigriventris), rice leaf miner (Agromyza oryzae), garden pea leaf miner (Chromatomyia horticola), tomato leaf miner (Liriomyza bryoniae), stone leek leaf miner (Liriomyza chinensis) , American serpentine leaf miner (Liriomyza trifolii), vegetable leaf miner (Liriomyza sativae), pea leaf miner (Liriomyza huidobrensis), onion maggot (Delia antiqua), onion maggot (Delia platura), beet leaf miner (Pegomya cunicularia), green bottle fly (Phormia regina), house fly (Musca domestica), mosquito (Culex pipiens pallens), malaria vector (Anopheles sinensis), Asian tiger mosquito (Aedes albopictus), mosquito (Culex pipiens molestus) and the like;
HYMENOPTERA such as cabbage sawfly (Athalia japonica), turnip sawfly (Athalia rosae ruficornis), apple argid sawfly (Arge mali) , large rose sawfly (Arge pagana), oriental chestnut gall wasp (Dryocosmus kuriphilus), wood ant (Formica japonica) and the like;
ACARINA such as broad mite (Polyphagotarsonemus latus), cyclamen mite (Steneotarsonemus pallidus), fungus mite (Tarsonemus waitei), straw itch mite (Pyemotes ventricosus), blue oat mite (Penthaleus major), citrus flat mite (Brevipalpus lewisi), privet mite (Brevipalpus obovatus), pineapple flat mite (Dolichotetranychus floridanus), persimmon false spider mite (Tenuipalpus zhizhilashviliae), flat mite (Brevipalpus phoenicis), Tuckerellid mite (Tuckerella pavoniformis), clover mite (Bryobia praetiosa), brown almond mite (Bryobia rubrioculus), apricot spider mite (Eotetranychus boreus), spider mite (Eotetranychus geniculatus), spider mite (Eotetranychus pruni), 6-spotted mite (Eotetranychus sexmanaculatus), tetranychid mite (Eotetranychus smithi), red spider mite (Eotetranychus uncatus), sugi spider mite (Oligonychus hondoensis), southern red mite (Oligonychus ilicis), larch mite (Oligonychus karamatus), citrus red mite (Panonychus citri), European red mite (Panonychus ulmi), carmine spider mite (Tetranychus cinnabarinus), tea red spider mite (Tetranychus kanzawai), 2-spotted spider mite (Tetranychus urticae), hawthorn spider mite (Tetranychus viennensis), pink tea rust mite (Acaphylla theae), tulip bulb mite (Aceria tulipae), pink citrus rust mite (Aculops pelekassi), plum rust mite (Aculus fockeui), apple rust mite (Aculus schlechtendali), ribbed tea mite (Calacarus carinatus), grape leaf rust mite (Calepitrimerus vitis), pear rust mite (Epitrimerus pyri), Japanese pear rust mite (Eriophyes chibaensis), flour mite (Acarus siro), brown legged grain mite (Aleuroglyphus ovatus), bulb mite (Rhizoglyphus robini), mould mite (Tyrophagus putrescentiae), tropical rat mite (Ornithonyssus bacoti), scrub typhus mite (Leptotrombidium akamushi), moth (Leptotrombidium scutellaris), chigger mite (Leptotrombidium pallidum) and the like;
TYLENCHIDA such as bent grass nematode (Anguina agrostis), ear-cockle nematode (Anguina tritici), potato rot nematode (Ditylenchus destructor), tobacco stunt nematode (Tylenchorhynchus claytoni), sugar cane stylet nematode (Tylenchorhynchus martini), stunt nematode (Tylenchorhynchus sp.) , rice root nematode (Hirschmanniella imamuri), rice root nematode (Hirschmanniella oryzae), coffee root-lesion nematode (Pratylenchus coffeae), lesion nematode (Pratylenchus convallariae), root lesion nematode (Pratylenchus fallax), root lesion nematode of tea (Pratylenchus loosi), California root lesion nematode (Pratylenchus neglectus), Cobb's root lesion nematode (Pratylenchus penetrans), plant root lesion nematode (Pratylenchus sp.), Steiner's spiral nematode (Helicotylenchus dihystera), grass spiral nematode (Helicotylenchus erythrinae), spiral nematode (Helicotylenchus sp.), lance nematode (Hoplolaimus sp.), reniform nematode (Rotylenchulus reniformis), British spiral nematode (Scutellonema brachyurum), oat nematode (Bidera avenae), cactus cyst nematode (Cactodera cacti), cyst nematode (Cryphodera sp.), gold-plated nematode (Globodera rostochiensis); Japanese cyst nematode (Heterodera elachista), soybean cyst nematode (Heterodera glycines), clover cyst nematode (Heterodera trifolii), peanut root-knot nematode (Meloidogyne arenaria), camellia root-knot nematode (Meloidogyne camelliae), root-knot nematode (Meloidogyne graminis), northern root-knot nematode (Meloidogyne hapla), southern root-knot nematode (Meloidogyne incognita), root-knot nematode (Meloidogyne sp.), citrus root nematode (Tylenchulus semipenetrans), fungivorous nematode (Aphelenchus avenae) and the like;
DORYLAIMIDA such as needle nematode (Longidorus martini), needle nematode (Longidorus sp.), American dagger nematode (Xiphinema americanum), dagger nematode (Xiphinema sp.), stubby root nematode (Trichodorus sp.) and the like;
THYSANURA such as oriental silverfish (Ctenolepisma villosa), silverfish (Lepisma saccharina), firebrat (Thermobia domestica) and the like;
ISOPTERA such as drywood termite (Cryptotermes domesticus), Formosan subterranean termite (Coptotermes formosanus), Japanese subterranean termite (Reticulitermes speratus), fungus-growing termite (Odontotermes formosanus) and the like;
PSOCOPTERA such as booklouse (Liposcelis bostrychophilus) and the like;
SIPHONAPTERA such as dog flea (Ctenocephalides canis) and the like;
ANOPLURA such as body louse (Pediculus humanus humanus) and the like;
CHILOPODA such as house centipede (Thereuronema tuberculata) and the like;
DIPLOPODA such as flat-backed millipede (Oxidus gracilis) and the like; and
MOLLUSCA such as terrestrial slug (Incilaria bilineata) and the like. - Furthermore, as such diseases, rice blast (Pyricularia oryzae) can be cited.
- As the application methods of the insecticidal and fungicidal composition of the present invention, there can be exemplified, for example, application to the plant itself (foliar spraying), application to the nursery box (nursery box application), application to the soil (soil treatments such as soaking into soil, mixture into soil, side dressing, dispersion on soil or spraying on soil) , application of paddy water (submerged application or rice field application), application to the seed (seed treatment) and the like.
- The insecticidal and fungicidal composition of the present invention is generally prepared into conveniently usable forms according to an ordinary manner for preparation of agricultural and horticultural chemicals. That is, the composition may be blended with a suitable inert carrier, optically along with an adjuvant, in a proper proportion and prepared into a suitable preparation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust, tablets or the like through dissolution, separation, suspension, mixing, impregnation, adsorption or adhering.
- The inert carrier which can be used in the present invention may be either solid or liquid. Such a material which can be an inert solid carrier includes, for example, soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residue of vegetables, synthetic polymers such as powdered synthetic resins, inorganic mineral powder such as lays (for example, kaolin, bentonite, acid clay and the like), talcs (for example, talc, pyrophyllite and the like), silica powders or flakes (for example, diatomaceous earth, silica sand, mica, white carbon [synthetic, high-dispersion silicic acid, also called finely divided hydrated silicon, hydrated silicic acid, some of commercially available products contain calcium silicate as the major component]), activated carbon, powdered sulfur, pumice stone, calcined diatomite, brick groats, fly ash, sand, calcium carbonate powder, calcium phosphate powder and other inorganic mineral powders, chemical fertilizers (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride and the like), compost and the like. These carriers can be used singly or in combination of two or more kinds.
- A material which can be the inert liquid carrier is selected from such a material which itself has solvency or which does not have such solvency but is capable of dispersing an effective ingredient compound with the aid of an adjuvant. The following are typical examples of the carrier and can be used singly or in combination of two or more kinds. Examples thereof include water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol and the like), ketones (for example, acetone, methylethyl ketone, methylisobutyl ketone, diisobutyl ketone, cyclohexanone and the like), ethers (for example, ethyl ether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran and the like), aliphatic hydrocarbons (for example, kerosene, mineral oil and the like), aromatic hydrocarbons (for example, benzene, toluene, xylene, solvent naphtha, alkyl naphthalene and the like), halogenated hydrocarbons (for example, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene and the like), esters (for example, ethyl acetate, butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate, dioctyl phthalate and the like), amides (for example, dimethylformamide, diethylformamide, dimethylacetamide and the like) and nitriles (for example, acetonitrile and the like).
- As an adjuvant, typical adjuvants mentioned below can be exemplified. These adjuvants can be used depending on purposes and used singly or in combination of two or more kinds or cannot be used at all in some cases.
- To emulsify, disperse, dissolve and/or wet a compound as an active ingredient, a surfactant is used. Examples thereof include surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonates, lignin sulfonates, higher alcohol sulfate esters and the like.
- Furthermore, to stabilize the dispersion of a compound as an active ingredient, adhere it and/or bind it, the following adjuvants can be used. Examples thereof include casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum Arabic, polyvinyl alcohols, pine oil, bran oil, bentonite, Xanthan gum, lignin sulfonates and the like.
- In order to improve the fluidity of a solid product, the following adjuvants can be used. For example, adjuvants such as waxes, stearates, alkyl phosphates and the like can be used. Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for suspendible products. As a defoaming agent, adjuvants such as silicon oils can also be used.
- Incidentally, the insecticidal and fungicidal composition of the present invention is stable to light, heat, oxidation and the like. However, an anti-oxidant or an ultraviolet absorber, for example, a phenol derivative such as BHT (2,6-di-t-butyl-4-methylphenol) and BHA (butylated hydroxyanisole), a bisphenol derivative or arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, condensates of phenetidine and acetone, or a stabilizer such as a benzophenone-based compound is added in a proper amount when necessary, whereby it is possible to obtain a composition with much stabilized effect.
- The weight ratio of the active compound in the present invention can be varied in a relatively wide range. The fungicidal active compound represented by the general formula (3) or (4) is contained from 0.02 to 50 weight parts and preferably from 0.1 to 20 weight parts per 1 weight part of the insecticidal active compound represented by the general formula (1) or (2). Furthermore, the content of the active ingredient of the insecticidal and fungicidal composition of the present invention is usually from 0.1 weight % to 20 weight % for dust formulation, from 5 weight % to 50 weight % for emulsifiable concentrate, from 10 weight % to 90 weight % for wettable powder, from 0.1 weight % to 20 weight % for granule, and from 10 weight % to 90 weight % for flowable formulation. On the other hand, the amount of the carrier in each formulation is usually from 60 weight % to 99 weight % for dust formulation, from 40 weight % to 95 weight % for emulsifiable concentrate, from 10 weight % to 90 weight % for wettable powder, from 80 weight % to 99 weight % for granule, and from 10 weight % to 90 weight % for flowable formulation. Meanwhile, the amount of the adjuvant is usually from 0.1 weight % to 20 weight % for dust formulation, from 1 weight % to 20 weight % for emulsifiable concentrate, from 0.1 weight % to 20 weight % for wettable powder, from 0.1 weight % to 20 weight % for granule, and from 0.1 weight % to 20 weight % for flowable formulation.
- In order to control various kinds of diseases and insect pests, the insecticidal and fungicidal composition of the present invention may be applied to crops which are expected to create diseases and insect pests or places where such creation is not desired in an amount effective in controlling diseases and insect pests as intact, as appropriately diluted with water or the like, or as suspended, and used accordingly. The amount thereof is varied according to various factors such as purpose, target diseases and insect pests, reared status of crops, occurrence trend of diseases and insect pests, weather, environmental conditions, the type of formulation, method of application, place of application, time of application and the like. However, generally, the active ingredient is preferably used at a concentration of from 0.0001 to 5000 ppm and preferably from 0.01 to 1000 ppm. Furthermore, the amount of the composition applied per 10 a is generally from 1 to 500 g as the active ingredient.
- The insecticidal and fungicidal composition of the present invention may be used singly for preventing various diseases and insect pests which are injurious to paddy rice, fruit trees, vegetables, other crops, flowers and the like. Also, it may be used in combination of one or more kinds of other insecticides and/or fungicides in order to obtain an excellent control effect.
- When the insecticidal and fungicidal composition of the present invention is used in combination with one or more kinds of other insecticides and/or fungicides, the insecticidal and fungicidal composition of the present invention may be used as a mixed solution with other insecticides and/or fungicides, or the insecticidal and fungicidal composition of the present invention may be used as a mixture with other insecticides and/or fungicides at the time of application of the agrochemicals. In addition to the above insecticides and fungicides, the insecticidal and fungicidal composition of the present invention can be used as a mixture with a plant protection agent such as a herbicide, a fertilizer, a soil conditioner, a plant growth regulator and the like or a material, whereby a multi-purpose composition with an excellent effect can be prepared.
- The typical examples for preparing the compound represented by the general formula (1) of the present invention are illustrated below with reference to the following Examples. However, the present invention is not restricted to these Examples.
- To a solution of 20.0 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 11.0 g of pyridine added to 100 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 13.0 g of 3-nitrobenzoyl chloride dissolved in 20 ml of tetrahydrofuran little by little. The reaction solution was stirred at room temperature for 10 hours, and then ethyl acetate and water were added thereto. Solution separation was performed for taking out an organic layer. The organic layer was dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with a mixed solvent of hexane and diisopropyl ether to obtain 26.0 g of the desired product (Yield: 85%) as a white solid.
1H-NMR (CDCl3,ppm) δ 2.33(6H, s), 7.37(2H, s), 7.68(1H, s), 7.72(1H, t, J = 8.1Hz), 8.28(1H, d, J = 8.1Hz), 8.94(1H, dd, J = 1.2, 8.1Hz), 8.75(1H, t, J = 1.2Hz) - To a solution of 0.90 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and 1.56 g of anhydrous stannous chloride added to 25 ml of ethanol and stirred at room temperature was added 2 ml of concentrated hydrochloric acid, and the resulting mixture was stirred at 60 degree centigrade for 1 hour. The reaction solution was returned to room temperature, poured into water, and then neutralized with potassium carbonate. Ethyl acetate was added thereto, the insoluble substance was filtered off, and then the organic layer was separated and dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with hexane to obtain 0.44 g of the desired product (Yield: 53%) as a white solid.
1H-NMR(CDCl3,ppm) δ 2.34(6H, s), 3.87(2H, broad), 6.86-6.89(1H, m), 7.20-7.35(6H, m) - To a solution of 0.25 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.06 g of pyridine added to 5 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 0.09 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran. The reaction solution was stirred at room temperature for 1 hour, and then ethyl acetate and 1N hydrochloric acid were added thereto for separating an organic layer. The organic layer was washed with saturated baking soda solution one time and then dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected and the solvent was removed under a reduced pressure to precipitate a solid. The precipitated solid was washed with diisopropyl ether to obtain 0.29 g of the desired product (Yield: 92%) as a white solid.
1H-NMR (DMSO-d6, ppm) 52.37 (6H, s), 7.34 (2H, s), 7.46-7.57 (4H, m), 7.75 (1H, d, J=7.8Hz), 7.98-8.01 (2H, m), 8.12 (1H, d, J=7.3Hz), 8.34 (1H, s), 8.87 (1H, s), 9.66 (1H, s). - To a solution of 0.18 g of 60% sodium hydride suspended in 15 ml of tetrahydrofuran was introduced dropwise 2.0 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide dissolved in 5 ml of tetrahydrofuran at room temperature. The reaction solution was stirred at room temperature for 30 minutes, and then 0.65 g of methyl iodide dissolved in 5 ml of tetrahydrofuran was introduced dropwise. Subsequently, the reaction solution was heated to 50 degree centigrade and stirred for 4 hours and then returned to room temperature, and ethyl acetate and water were added thereto. An organic layer was separated, washed with water one time, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 6:1) to obtain 1.73 g of the desired product (Yield: 84%) as a white solid.
1H-NMR(CDCl3,ppm) δ2.31(6H, s), 3.38(3H, s), 7.27(2H, s), 7.37(1H, t, J = 7.8Hz), 7.62-7.65(1H, m), 8.05(1H, t, J = 2.0Hz), 8.11-8.14(1H, m). - A solution of 1.50 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-nitrobenzamide and 0.15 g of 10% palladium carbon added to 20 ml of methanol was stirred in an ordinary pressure, in a hydrogen atmosphere for 2 hours. The catalyst was filtered out and then the solvent was removed under a reduced pressure. Subsequently, the precipitated solid was washed with hexane to obtain 1.24 g of the desired product (Yield: 88%) as a white solid.
1H-NMR(CDCl3, ppm) δ2.27(6H, s), 3.31(3H, s), 3.80 (2H, broad), 6.40-6.43 (1H, m), 6.54-6.58(1H, m), 6.71(1H, t, J = 2.0Hz), 6.76-6.86(1H, m), 7.22(2H, s). - A desired title product was prepared according to the conditions as described in Example 1-3 as a white solid.
1H-NMR(DMSO-d6,ppm) δ2.29(6H, s), 3.24(3H, s), 6.84(1H, d, J = 7.8Hz), 7.12(1H, t, J = 7.8Hz), 7.33(2H, s), 7.50-7.64(4H, m), 7.85-7.88(2H, m), 7.98-8.03(1H, m), 10.22(1H, s). - To a solution of 0.6 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.4 g of pyridine added to 10 ml of tetrahydrofuran was added 0.35 g of 2-chloronicotic acid chloride hydrochloride, and the resulting solution was stirred at room temperature for 4 hours. Ethyl acetate was added thereto and then the reaction solution was washed with saturated baking soda solution two times, and the solvent was removed under a reduced pressure. The precipitated solid was washed with a mixed solvent of hexane and diisopropyl ether and dried to obtain 0.64 g of the desired product (Yield: 75%) as a white solid.
1H-NMR(DMSO-d6,ppm) δ2.30 (6H, s), 7.45 (2H, s), 7.54-7.60 (2H, m), 7.77-7.80 (1H, m), 7.95 (1H, d, J= 7.8Hz), 8.10-8.12 (1H, m), 8.30 (1H, s), 8.54-8.59 (1H, m), 10.03 (1H, s), 10.88 (1H, s). - A solution of 99 mg of nicotic acid and 153 mg of 1,1'-oxalyldiimidazole added to 10 ml of acetonitrile was stirred at room temperature for 15 minutes and at 40 degree centigrade for 40 minutes. The reaction solution was returned to room temperature, and then 300 mg of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide was added thereto and stirred at 60 degree centigrade for 5 hours. Subsequently, the solvent was removed under a reduced pressure to obtain a residue. While ethyl was added to the resulting residue, the organic layer was washed with saturated baking soda solution two times, and the solvent was removed under a reduced pressure again. The obtained residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 1:3) to obtain 70 mg of the desired product (Yield: 18%) as a white solid.
1H-NMR(DMSO-d6,ppm) δ2.30 (6H, s), 7.45 (2H, s), 7.54-7.61 (2H, m), 7.78 (1H, d, J = 8.3Hz), 8.06 (1H, d, J = 7.3Hz), 8.32-8.35 (2H, m), 8.77-8.79 (1H, m), 9.14 (1H, d, J = 1.5Hz), 10.00 (1H, s), 10.66 (1H, s). - To a solution of 1.0 g of N-methyl-4-heptafluoroisopropyl-2-methylaniline added to 5 ml of N,N-dimethylformamide was introduced dropwise 0.8 g of N-bromosuccinic acid imide dissolved in 3 ml of N,N-dimethylformamide. The resulting solution was stirred at room temperature for 5 hours, and then ethyl acetate and water were added thereto for separating an organic layer. The organic layer was washed with water two times, and then dried over anhydrous magnesium sulfate and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 9:1) to obtain 0.86 g of the desired product (Yield: 68%) as red oil.
1H-NMR (CDCl3, ppm) 52.41 (3H, s), 2.93 (3H, s), 3.90 (1H, broad), 7.23 (1H, s), 7.54 (1H, s). - A desired title product was prepared from N-methyl-2-bromo-4-heptafluoroisopropyl-6-methylaniline according to the conditions as described in Example 1 as a white solid.
1H-NMR(DMSO-d6,ppm) δ2.41(3H, s), 3.25(3H, s), 6.95(1H, dd, J = 1.5,7.8Hz), 7.16(1H, t, J = 7.8Hz), 7.50-7.64(4H, m), 7.68(1H, s), 7.86-7.88(2H, m), 7.93(1H, t, J = 1.5Hz), 7.98-8.00(1H, m), 10.24(1H, s). - To a solution of 40 mg of 60% sodium hydride suspended in 10 ml of tetrahydrofuran was introduced dropwise 0.3 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-(benzoylamino)benzamide dissolved in 5 ml of tetrahydrofuran at room temperature. The reaction solution was stirred at room temperature for 1 hour, and then 0.16 g of methyl iodide dissolved in 5 ml of tetrahydrofuran was introduced dropwise. Subsequently, the reaction solution was heated to 50 degree centigrade, stirred for 4 hours and then returned to room temperature, and ethyl acetate and water were added thereto. An organic layer was separated and washed with water one time, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure. The resulting residue was washed with diisopropyl ether to obtain 1.73 g of the desired product (Yield: 84%) as a white solid.
1H-NMR (DMSO-d6, ppm) δ2.20 (6H, s), 3.08 (3H, s), 3.20 (3H, s), 6.93-7.39 (10H, m), 7.45-7.51 (1H, m). - 0,35 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.19 g of a Lawson reagent were added to 10 ml of toluene, and the resulting solution was heated and stirred at a reflux temperature for 6 hours. The reaction solution was concentrated under a reduced pressure for removing the solvent, and then the resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 3:1) to obtain 0.07 g of the desired product (Yield: 20%).
1H-NMR (CDCl3,ppm) δ2.36 (6H, s) , 3.87 (2H, broad-s), 6.89-6.87 (1H, m), 7.18-7.24 (2H, m), 7.33 (1H, s), 7.39 (2H, s), 8.56 (1H, broad-s). - A desired title product was prepared from N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzthioamide according to the conditions as described in Example 1-3.
1H-NMR (CDCl3,ppm) δ2.38 (6H, s), 7.25-8.00 (11H, m), 8.34 (1H, s), 8.85 (1H, broad.). - A solution of 0.37 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzoylamino)benzamide and 0.30 g of a Lawson reagent added to 10 ml of toluene was stirred at 70 degree centigrade for 6 hours. The reaction solution was concentrated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 3:1) to prepare 0.18 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(phenylthiocarbonylamino)benzamide (Yield: 47%) and 0.05 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(phenylthiocarbonylamino)benzthioamide (Yield: 13%) respectively.
Physical properties of Compound No. 2202
1H-NMR (CDCl3, ppm) δ2.36 (6H, s), 7.37 (2H, s), 7.47-7.61(5H, m), 7.85-8.03 (4H, m), 8.57 (1H, s), 9.18 (1H, s).
Physical properties of Compound No. 2203
1H-NMR (CDCI3, ppm) δ2.38 (6H, s), 7.41 (2H, s), 7. 45-7. 55 (4H, m), 7.90-7.96 (4H, m), 8.57 (1H, broad),8.74 (1H,broad), 9.18(1H,broad). - Using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and benzyl bromide, a desired title product was prepared according to the method as described in Example 6.
- Using N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and 2-fluorobenzoyl chloride, a desired title product was prepared according to the method as described in Examples 1-2 and 1-3.
- Using N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(2-fluorobenzoylamino)benzamide and ethyl iodide, a desired title product was prepared according to the method as described in Example 6.
- A solution of 1.07 g of N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[N-ethyl-N-(2-fluorobenzoyl)amino]benzamide and 0.15 g of 10% palladium carbon added to 10 ml of methanol was stirred at 45 degree centigrade in a hydrogen atmosphere for 6 hours. The catalyst was filtered out and then the solvent was removed under a reduced pressure. Subsequently, the resulting residue was purified by silica gel (NH Silica by Fuji Silysia Chemical Ltd.) column chromatography using an eluent (development solvent; hexane : ethyl acetate = 1:1) to obtain 0.30 g of the desired product (Yield: 32%) as a white solid.
1H-NMR (DMSO-d6, ppm)δ1.17 (3H, broad), 2.22 (6H, s), 3.94 (2H, broad), 7.01-7.08 (2H, m), 7.29-7.43 (6H, m), 7.72-7.77 (2H, m), 9.90 (1H, s). - 2.35 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-chloro-3-nitrobenzamide prepared in accordance with the method as described in Example 1-1 and 0.87 g of potassium fluoride (spray drying product) were added to 25 ml of N,N-dimethylformamide dried using molecular sieves, and the mixture was heated and stirred at 150 degree centigrade for 3 hours. The reaction solution was returned to room temperature, and then ethyl acetate and water were added thereto for solution separation. An organic layer was separated, washed with water two times, and dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate =4:1) to obtain 1. 02 g of the desired product (Yield: 45%) as a solid.
1H-NMR (CDCl3, ppm) δ 2.37 (6H, s), 7.39 (2H, s), 7.48-7.53 (1H, m), 7.87 (1H, d, J = 11.5Hz ), 8.23-8.28 (1H, m), 8.42-8.46 (1H, m) . - A desired title product was prepared according to the method as described in Examples 1-2 and 1-3.
1H-NMR (DMSO-d6,ppm) δ 2.34(6H, s), 7.37(1H, t, J = 7.8Hz), 7.45(2H, s), 7.53-7.65(4H, m), 7.77-7.82(1H, m), 8.00-8.02(2H, m), 10.10(1H, s), 10.29(1H, s). - 5.22 g of 4-fluoro-3-nitrobenzoic acid and 0.1 g of N, N-dimethylformamide were introduced to 30 ml of toluene, and then 3.7 g of thionyl chloride was added thereto. The resulting solution was stirred at 80 degree centigrade for 1 hour and then stirred under a reflux condition for 2 hours. The solution was cooled down to room temperature, the solvent was removed under a reduced pressure, the resulting residue was dissolved in 10 ml of tetrahydrofuran, and added dropwise to a mixed solution of 8.1 g of 2,6-dimethyl-4-heptafluoroisopropylaniline, 4.4 g of pyridine and 20 ml of tetrahydrofuran. The solution was stirred at room temperature for 2 hours, and then ethyl acetate was introduced thereinto. The organic layer was washed successively with water and saturated baking soda solution, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 4: 1) to obtain 5.9 g of the desired product (Yield: 46%) as a white solid.
1H-NMR(CDCl3,ppm) δ2.11(6H, s), 7.26-7.31(3H, m), 8.12-8.15(1H, m), 8.60-8.62(1H, m), 8.70(1H, s). - A desired title product was obtained according to the conditions as described in Example 1-2 as a white solid.
1H-NMR(DMSO-d6,ppm) δ2.26(6H, s), 5.42(2H, broad-s), 7.10-7.19(2H, m) , 7.37(1H, dd, J = 2.0,8.8Hz) , 7.42(2H, s) , 9.78(1H, s) . - 18 ml of 98% sulfuric acid was cooled from 0 to 5 degree centigrade and stirred, and 2.50 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-amino-4-fluorobenzamide was added thereto. The reaction solution was stirred for 15 minutes, and then 18 ml of 37% aqueous formaldehyde solution was added dropwise thereto. The solution was stirred at 0 degree centigrade for 1 hour and at room temperature for 3 hours. To the reaction solution cooled down to 0 degree centigrade again was added 28% ammonia water for neutralization and ethyl acetate was added thereto for separating an organic layer. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 4:1) to obtain 1.74 g of the desired product (Yield: 67%) as an amorphous substance.
1H-NMR(CDCl3, ppm) δ2.32(6H, s), 2.94(3H, d, J = 4.9Hz), 4.14(1H, broad), 7.03(1H, dd, J = 8.3,11.2Hz), 7.10-7.13(1H, m), 7.24(1H, s), 7.34(2H, s), 7.42(1H, s). - The following compounds can be prepared in accordance with the method as described in Example 11-3.
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-(methylamino)benzamide
1H-NMR(DMSO-d6) δ 2.32(6H, s), 2.76(3H, d, J = 4.9Hz), 5.84(1H, broad), 6.77-6.81(2H, m), 7.10(1H, t, J = 7.8Hz), 7.43(2H, s), 9.90(1H, s).
N-[2,6-dimethyl-4-(nonafluoro-2-butyl)]phenyl 2-fluoro-3-(methylamino)benzamide
1H-NMR(DMSO-d6) δ 2.32(6H, s), 2.77(3H, d, J = 4.9Hz), 5.82(1H, broad), 6.79(1H, t, J = 7.8Hz), 7.08-7.21(2H, m), 7.42(2H, s), 9.88(1H, s).
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 2-fluoro-3-(methylamino)benzamide
1H-NMR(DMSO-d6) δ 2.33(6H, s), 2.76(3H, d, J= 4.9Hz), 4.55(3H, s), 6.58-6.62(1H, m), 6.70-6.78(1H, m), 7.13(1H, t, J = 7.8Hz), 7.31(1H, s), 7.50(2H, s). - Using 4-nitrobenzoyl chloride, a desired title product was obtained according to the conditions as described in Example 1-3 as a white solid.
1H-NMR(DMSO-d6, ppm) δ2.23(6H, s), 3.42 (3H, s), 7.41(1H, broad), 7.45(2H, s), 7.60(2H, broad), 7.90(1H, broad), 8.08-8.13(3H, broad), 9.93(1H, s). - To a solution of 2.0 g of 4-heptafluoroisopropylaniline added to 5 ml of N,N-dimethylformamide was introduced 2.73 g of N-bromosuccinic acid imide dissolved in 10 ml of N,N-dimethylformamide at 5 degree centigrade. The reaction solution was returned to room temperature and stirred for 2 hours, and then ethyl acetate and water were added thereto for separating an organic layer. The organic layer was further washed with water one time. After the solvent was removed under a reduced pressure, the resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 20:1) to obtain 2.20 g of the desired product (Yield: 69%) as orange oil.
1H-NMR(CDCl3,ppm) δ4.89(2H, broad-s), 7.59(2H, s). - A mixed solution of 2.20 g of 2,6-dibromo-4-heptafluoroisopropylaniline, 1.46 g of 3-nitrobenzoyl chloride and 10 ml of pyridine was stirred at 70 degree centigrade for 20 hours. The resulting solution was returned to room temperature, and then ethyl acetate and IN hydrochloric acid were added thereto. An organic layer was separated and then washed with saturated baking soda solution. The solvent was removed under a reduced pressure and the resulting residue was dissolved in a mixed solvent of 8 ml of tetrahydrofuran and 2 ml of methanol. Subsequently, the reaction solution was cooled down to 5 degree centigrade, 0.30 g of sodium hydroxide was added thereto, the mixture was stirred for 2 hours, and then ethyl acetate and water were added thereto. An organic layer was separated and washed with saturated baking soda solution, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with hexane to obtain 2.19 g of the desired product (Yield: 73%) as a light brown solid.
1H-NMR(DMSO-d6,ppm) δ7.92(1H, t, J = 7.8Hz), 8.08(2H, s), 8.45(1H, d, J = 7.8Hz), 8.53(1H, dd, J 1. 5, 7. 8Hz) , 8.85(1H, d, J = 1.5Hz), 11.08(1H, s). - A desired title product was obtained according to the conditions as described in Example 1-2 as a white solid.
1H-NMR(DMSO-d6, ppm) δ5.39(2H, broad-s), 6.77-6.80(1H, m), 7.13-7.20(3H, m), 8.02(2H, s), 10.35(1H, s). - Using 2-fluorobenzoyl chloride, a desired title product was obtained according to the conditions as described in Example 1-3 as a white solid.
1H-NMR (DMSO-d6, ppm) δ7.33-7.40(2H, m), 7.55-7.63(2H, m), 7.68-7.72(1H, m), 7.78(1H, d, J = 7.8Hz), 7.99(1H, d, J = 7.8Hz), 8.05(2H, s), 8.34(1H, s), 10.65(1H, s), 10.69(1H, s). - To 20 ml of an acetonitrile solution of 1.25 g of 4-aminothiophenol and 1.11 g of triethylamine was added 5.91 g of 1-iodoheptafluoro-n-propane. The resulting mixture was stirred at room temperature for 3 hours, diluted with ether, and then washed with aqueous 1N sodium hydroxide solution, and purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 4: 1) to obtain 1.85 g of the desired product (Yield: 63%).
1H-NMR(CDCl3, ppm) δ 3.95 (2H, s), 6.66(2H, d, J=8.8Hz), 7.40(2H, d, J = 8.8Hz). - To a solution of 0.77 g of 4-(heptafluoro-n-propylthio) aniline added to 15 ml of N,N-dimethylformamide was introduced 0.98 g of N-bromosuccinic acid imide. The resulting solution was stirred at 60 degree centigrade for 2 hours, and then ether and water were added thereto for separating an organic layer. The organic layer was washed with water two times, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 9:1) to obtain 1.19 g of the desired product (Yield: 100%) as red oil.
1H-NMR(CDCl3, ppm) δ4.98(2H, broad-s), 7.66(2H, s). - To a solution of 1.08 g of 2,6-dibromo-4-(heptafluoro-n-propylthio)aniline and 0.4 g of pyridine added to 20 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 0.55 g of 3-nitrobenzoyl chloride dissolved in 20 ml of tetrahydrofuran little by little. The reaction solution was stirred at room temperature for 10 hours, and then ethyl acetate and water were added thereto. An organic layer was separated and dried over anhydrous magnesium sulfate. The solution was filtered out, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 4:1) to obtain 0.86 g of the desired product (Yield: 48%) as a white solid.
1H-NMR(CDCl3,ppm) δ7.73(1H, s, J = 7.8Hz), 7.77(1H, t, J = 7.8Hz), 7.96(2H, s), 8.31(1H, s) , 8.47-8.50(1H, m), 8.79(1H, t, J = 2.0Hz). - To a solution of 0.97 g of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide and 0.95 g of anhydrous stannous chloride added to 20 ml of ethanol and stirred at room temperature was added 2 ml of concentrated hydrochloric acid, and the resulting mixture was heated and stirred at 60 degree centigrade for 1 hour. The reaction solution was returned to room temperature, poured into water, and then neutralized with potassium carbonate. Ethyl acetate was added thereto, the insoluble substance was filtered out, and then an organic layer was separated and dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with hexane to obtain 0.75 g of the desired product (Yield: 81%) as a white solid.
1H-NMR(CDCl3,ppm) δ3.89(2H, broad-s), 6.90(1H, dt, J = 2.5,6.4Hz), 7.28-7.30(3H, m), 7.60(1H, s), 7.93(2H, s). - To a solution of 0.10 g of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-aminobenzamide and 0.02 g of pyridine added to 5 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 0.03 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran. The resulting mixture was stirred at room temperature for 1 hour, and then ethyl acetate and 1N hydrochloric acid were added thereto for separating an organic layer. The organic layer was washed with saturated baking soda solution one time and then dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 3:1) to obtain 0.10 g of the desired product (Yield: 67%) as a white solid.
1H-NMR (CDCl3, ppm) δ7.47-7.57 (4H, m), 7.78 (1H, d, J = 7.8Hz), 7.93 (2H, s), 7.99-8.01 (2H, m), 8.18 (1H, d, J=7.8Hz), 8.33 (1H, t, J = 2.0Hz), 9.27 (1H, s), 9.65 (1H, s). - To a solution of 0.15 g of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-aminobenzamide and 0.03 g of pyridine added to 5 ml of tetrahydrofuran was added 0.05 g of 2-chloronicotic acid chloride hydrochloride, and the mixture was stirred at room temperature for 4 hours. Ethyl acetate was added thereto, and then the solution was washed with saturated baking soda solution two times, and the solvent was removed under a reduced pressure. The precipitated solid was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 3:1) to obtain 0.17 g of the desired product (Yield: 92%) as an amorphous substance.
1H-NMR(CDCl3,ppm) δ7.44 (1H, dd, J = 4.8, 7.8Hz), 7.56 (1H, t, J = 7.8Hz), 7.80 (1H, d, J = 7.8Hz), 7.86 (1H, s), 7.92 (1H, d, J= 7.8Hz), 7.95(2H, s), 8.23 (1H, dd, J = 2.0., 7.8Hz), 8.30 (1H, s), 8.41 (1H, s), 8.55 (1H, dd, J = 2.0, 4.5Hz). - To a solution of 0.5 g of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-nitrobenzamide added to 15 ml of chloroform and stirred at room temperature was introduced 0.5 g of m-chloroperbenzoic acid. The mixture was stirred at room temperature for 2 days, and then an aqueous solution of sodium sulfite was added thereto and stirred. While solution separation was performed, the reaction solution was washed with aqueous sodium hydroxide solution and saturated salt water, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 4 : 1) to obtain 0. 36 g of the desired product (Yield: 70%) as a white solid.
1H-NMR(CDCl3, ppm) δ7.76-7.82 (2H, m), 8.06 (1H, s), 8.29 (1H, s), 8.33-8.35 (1H, m), 8.49-8.53 (1H, m), 8.81 (1H, s). - Using N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-nitrobenzamide, a desired title product was obtained according to the method as described in Example 1-2.
1H-NMR(CDCl3,ppm) δ6.90-6.94 (1H, m), 7.28-7.33 (3H, m), 7.73 (1H, s), 8.02 (1H, s), 8.25 (1H, s). - Using N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-aminobenzamide, a desired title product was obtained according to the method as described in Example 1-3.
1H-NMR(CDCl3,ppm) δ7.45-7.61 (4H, m), 7.77-7.79 (1H, m), 7.87-7.91 (3H, m), 8.01 (1H, s), 8.07-8.10 (1H, m), 8.15 (1H, s), 8.25 (1H, s), 8.38 (1H, s) - 3.0 g (1.3 mmole) of 2,6-dibromo-4-heptafluoro-n-propylthioaniline, 3.0 g (21.9 mmole) of potassium carbonate, 0.75 g (0.65 mmole) of tetrakis(triphenylphosphine)palladium and 0.17 g (1.3 mmole) of trimethylboroxin were added to 20 ml of DMF, and the resulting solution was stirred at 135 degree centigrade for 6 hours. The reaction solution was returned to room temperature, and then the insoluble substance was removed with celite, and the filtrate was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 12:1 to 4:1) to obtain 1.17 g of the desired product (Yield: 55%) as oil.
1H-NMR(CDCl3,ppm) δ2.17(6H, s), 3.86(2H, broad-s), 7.22(2H, s). - A mixture of 20.0 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide, 4.40 g of 37% aqueous formaldehyde solution, 2.0 g of 10% palladium carbon and 200 ml of ethyl acetate was stirred in an ordinary pressure, in a hydrogen atmosphere at room temperature. An insoluble substance of the reaction solution was filtered out and the filtered product was washed with ethyl acetate. The filtrate was collected and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with diisopropyl ether to obtain 13.5 g of the desired product (Yield: 65%) as a white solid.
1H-NMR(CDCl3, ppm) δ2.35(6H, s), 2.91(3H, s), 6.82(1H, d, J = 7.3Hz), 7.18-7.52(7H, m). - To a solution of 1.37 g of 3-aminobenzoic acid and 0.4 g of sodium hydroxide added to 50 ml of water was added dropwise a solution of 1.41 g of benzoyl chloride and 0.4 g of sodium hydroxide dissolved in 5 ml of water under an ice bath at the same time, and the resulting mixture was stirred at room temperature for 6 hours. 1N hydrochloric acid was added to the reaction solution which was adjusted to pH 1, and then the precipitated solid was filtered off and collected to obtain 1.92 g of the desired product (Yield: 80%) as a white solid.
1H-NMR(CDCl3, ppm) δ7.40-7.56 (5H, m), 7.78(1H, d, J=7.8Hz), 8.00(2H, d, J=8.3Hz), 8.15(1H, d, J=7.8Hz), 8.35(1H, t, J=2.0Hz), 9.89(1H, s). - To a solution of 1.5 g of 3-(benzoylamino)benzoic acid suspended in 10 ml of toluene was added 2 ml of thionyl chloride and the resulting mixture was stirred under a reflux condition for 2 hours. The reaction solution was returned to room temperature, and then the solvent was removed under a reduced pressure to obtain 1.53 g of the desired product (Yield: 95%) as a white solid.
1H-NMR(CDCl3,ppm) δ 7.51-7.62(4H, m), 7.90(2H, d, J = 7.3Hz), 7.93(1H, s), 7.97(1H, s), 8.15(1H, dt, J = 1.0,5.9Hz), 8.28(1H, t, J = 2.0Hz). - Using benzoic acids which can be easily available, the following compounds can be prepared in accordance with the methods as described in Examples 15-1 and 15-2.
3-[(2-fluorobenzoyl)amino]benzoic acid chloride
3-[(3-fluorobenzoyl)amino]benzoic acid chloride
3-[(4-fluorobenzoyl)amino]benzoic acid chloride
3-[(2-chlorobenzoyl)amino]benzoic acid chloride
3-[(3-chlorobenzoyl)amino]benzoic acid chloride
3-[(4-chlorobenzoyl)amino]benzoic acid chloride
3-[(3-cyanobenzoyl)amino]benzoic acid chloride
3-[(4-cyanobenzoyl)amino]benzoic acid chloride
3-[(2-methylbenzoyl)amino]benzoic acid chloride
3-[(3-methylbenzoyl)amino]benzoic acid chloride
3-[(4-methylbenzoyl)amino]benzoic acid chloride
3-[(2-nitrobenzoyl)amino]benzoic acid chloride
3-[(3-nitrobenzoyl)amino]benzoic acid chloride
3-[(4-nitrobenzoyl)amino]benzoic acid chloride
3-[(2-trifluoromethylbenzoyl)amino]benzoic acid chloride
3-[(3-trifluoromethylbenzoyl)amino]benzoic acid chloride
3-[(4-trifluoromethylbenzoyl)amino]benzoic acid chloride
3-[(2-trifluoromethoxybenzoyl)amino]benzoic acid chloride
3-[(3-trifluoromethoxybenzoyl)amino]benzoic acid chloride
3-[(4-trifluoromethoxybenzoyl)amino]benzoic acid chloride
3-[(2,3-difluorobenzoyl)amino]benzoic acid chloride
3-[(2,4-difluorobenzoyl)amino]benzoic acid chloride
3-[(2,5-difluorobenzoyl)amino]benzoic acid chloride
3-[(2,6-difluorobenzoyl)amino]benzoic acid chloride
3-[(3,4-difluorobenzoyl)amino]benzoic acid chloride
3-[(pyridine-3-yl)carbonylamino]benzoic acid chloride
3-[(2-fluoropyridine-3-yl)carbonylamino]benzoic acid chloride
3-[(2-chloropyridine-3-yl)carbonylamino]benzoic acid chloride
3-[(2,4-dichlorobenzoyl)amino]benzoic acid chloride
3-[(2,6-dichlorobenzoyl)amino]benzoic acid chloride
3-[(3,4-dichlorobenzoyl)amino]benzoic acid chloride
3-[(2-chloro-4-fluorobenzoyl)amino]benzoic acid chloride
3-[(4-chloro-2-fluorobenzoyl)amino]benzoic acid chloride
3-[(2-chloro-6-fluorobenzoyl)amino]benzoic acid chloride
3-[(2,3,6-trifluorobenzoyl)amino]benzoic acid chloride - To a solution of 0.1 g of 2,6-dimethyl-4-(heptafluoro-n-propylthio)aniline and 0.03 g of pyridine added to 5 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 0.09 g of 3-(benzoylamino)benzoic acid chloride dissolved in 1 ml of tetrahydrofuran. The resulting mixture was stirred at room temperature for 1 hour, and then ethyl acetate and 1N hydrochloric acid were added thereto for separating an organic layer. The organic layer was washed with saturated baking soda solution one time and then dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 3:1) to obtain 0.10 g of the desired product (Yield: 53%) as a white solid.
1H-NMR(CDCl3,ppm) δ2.31(6H, s), 7.41(2H, s), 7.50-7.67(5H, m), 7.71(1H, d, J=7. 8Hz), 7.87-7.90(3H, m), 8.07(1H, s), 8.31(1H, s). - While 24.4 g of 2,6-dimethylaniline and 50.0 g of hexafluoroacetone hydrate were mixed at room temperature, 0.5 g of p-toluenesulfonic acid monohydrate was added thereto. The reaction solution was stirred at 100 degree centigrade. After disappearance of the starting raw material was confirmed by means of TLC, to the reaction solution were added ethyl acetate and 1N aqueous sodium hydroxide solution for solution separation and extraction. Anhydrous magnesium sulfate was added to an organic layer, and the organic layer was dried and then filtered off. The filtrate was concentrated under a reduced pressure, and then hexane was added to the residue for washing. The suspension was filtered off and the resulting filtered product was vacuum-dried at room temperature to obtain 24.3 g of the desired product (Yield: 69%) in the form of powder.
1H-NMR(CDCl3,ppm) δ2.20(6H, s), 3.26(1H, broad-s), 3.76(2H, broad-s), 7.25(2H, s). - At room temperature, 5.0 g of 2,6-dimethyl-4-[1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)e thyl]aniline, 3.9 g of 3-nitrobenzoyl chloride and 2.1 g of pyridine were introduced to 50 ml of tetrahydrofuran in a reaction vessel, and the resulting mixture was stirred at room temperature. After disappearance of the starting raw material was confirmed by means of TLC, to the reaction solution was added saturated baking soda solution and stirred for a while. Subsequently, ethyl acetate and water were added to the reaction solution for solution separation. Anhydrous magnesium sulfate was added to the separated organic layer, the organic layer was dried and filtered off. The filtrate was evaporated to dryness and the resulting solid was pulverized to obtain 7.5 g of the desired product (Yield: 95%) in the form of powder.
1H-NMR(DMSO-d6,ppm) δ2.26(6H, s), 7.46(2H, s), 7.88(1H, t, J = 7.8Hz) , 8.43-8.48(2H, m), 8.73(1H s), 8.81(1H, s), 10.27(1H, s). - A solution of 8.0 g of N-[2,6-dimethyl-4-(1-hydroxy-2,2,2-trifluoro-1-(trifluoromethy l)ethyl}phenyl] 3-nitrobenzamide and 0.8 g of 10% palladium carbon added to 50 ml of methanol was stirred in a hydrogen atmosphere at room temperature. After disappearance of the starting raw material was confirmed by means of TLC, the reaction solution was filtered off and the obtained filtrate was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 3:1) to obtain 6. 3 g of the desired product (Yield: 85%) in the form of powder.
1H-NMR(DMSO-d6,ppm) δ2.35(6H, s), 4.31(2H, broad), 6.84-6.87(1H, m), 7.21-7.25(1H, m), 7.29-7.31(2H, m), 7.47-7.49(2H, m), 7.83(1H, s), 8.94(1H, s). - At room temperature, 6.0 g of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethy 1)ethyl}phenyl] 3-aminobenzamide, 2.5 g of benzoyl chloride and 1.8 g of pyridine were introduced to 50 ml of tetrahydrofuran. After disappearance of the starting raw material was confirmed by means of TLC, the reaction solution was filtered off and the obtained filtrate was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate = 3:1) to obtain 6.3 g of the desired product (Yield: 85%) in the form of powder.
1H-NMR(DMSO-d6,ppm) δ2.26(6H, s), 7.44(2H, s), 7.51-7.63(4H, m), 7.74(1H, d, J = 7.8Hz), 7.98-8.07(3H, m), 8.35(1H, s), 8.71(1H, s), 9.90(1H, s), 10.47(1H, s). - Using 2-fluorobenzoyl chloride instead of benzoyl chloride, N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethy l)ethyl}phenyl] 3-[(2-fluorobenzoyl)amino]benzamide was prepared according to Example 16-4.
1H-NMR(DMSO-d6, ppm) δ2.34(6H, s), 7.21(1H, dd, J=8.2,11.2Hz), 7.32(1H, t, J = 7.8Hz), 7.49-7.56(4H, m), 7.78(1H, d, J = 7.8Hz), 8.04-8.08(2H, m), 8.23(1H, s), 8.71(1H, s), 9.08(1H, d, J = 11.2Hz). - At room temperature, 8.0 g of N-[2,6-dimethyl-4-(1-hydroxy-2,2,2-trifluoro-1-(trifluoromethy 1)ethyl}phenyl] 3-(benzoylamino)benzamide and 1.0 g of pyridine were introduced to 40 ml of thionyl chloride. Thereafter, the mixture was heated and stirred under a reflux condition. After disappearance of the starting raw material was confirmed by means of TLC, the reaction solution was cooled down and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane : ethyl acetate =3:1) to obtain 6.2 g of the desired product (Yield: 75%) in the form of powder.
1H-NMR(DMSO-d6, ppm) δ2.34(6H, s), 7.49-7.63(6H, m), 7.76(1H, d, J = 7.8Hz), 7.99-8.08(3H, m), 8.37(1H, s), 9.99(1H, s), 10.48(1H, s). - At room temperature, 300 mg of N-[2,6-dimethyl-9-(1-chloro-2,2,2-trifluoro-1-(trifluoromethyl )ethyl}phenyl] 3-(benzoylamino)benzamide and 165 mg of potassium fluoride were introduced to 20 ml of N,N-dimethylformamide. Thereafter, the mixture was heated to 120 degree centigrade and stirred for 4 hours. After the reaction solution was cooled down to room temperature, ethyl acetate and water were added thereto for separating an organic layer. Anhydrous magnesium sulfate was added thereto, the organic layer was dried and filtered off, and the filtrate was concentrated under a reduced pressure. The resulting residue was washed with diisopropyl ether. The suspension was filtered off and the obtained filtered product was vacuum-dried at room temperature to obtain 250 mg of the desired product (Yield: 85%) in the form of powder. The physical properties were described in Example 1-3.
- At room temperature, 2.0 g of 2,6-dimethyl-4-[1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)e thyl]aniline, 2.7 g of 3-(benzoylamino)benzoyl chloride and 1.2 g of pyridine were introduced to 50 ml of tetrahydrofuran, and the resulting solution was stirred at room temperature. After disappearance of the starting raw material was confirmed by means of TLC, saturated baking soda solution was added to the reaction solution and the mixture was stirred for a while. Ethyl acetate and water were added to the reaction solution for solution separation. To the separated organic layer was added anhydrous magnesium sulfate, and the organic layer was dried and filtered off. The filtrate was evaporated to dryness under a reduced pressure and the resulting solid was pulverized to obtain 3.4 g of the desired product (Yield: 95%) in the form of powder. The physical properties were described in Example 16-4.
- At room temperature, 300 mg of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethy 1)ethyl}phenyl] 3-(benzoylamino)benzamide was introduced to 20 ml of methylene chloride. Next, 480 mg of 2,2-difluoro-1,3-dimethyl-2-imidazolidinone was added dropwise thereto and stirred at room temperature for 8 hours. Water was added to the reaction solution and an organic layer was separated. Anhydrous magnesium sulfate was added thereto, and the organic layer was dried and filtered off. The obtained filtrate was evaporated to dryness under a reduced pressure and the resulting solid was pulverized to obtain 180 mg of the desired product (Yield: 60%) in the form of powder. The physical properties were described in Example 1-3.
- Next, typical formulation examples of the present invention will be illustrated. However, the present invention is not restricted to these formulation examples. Incidentally, in the formulation examples, part(s) refers to weight part(s).
- 30 parts of the compound (3006), 3 parts of the compound (1245), 22 parts of bentonite, 42 parts of talc and 3 parts of Sorpol 5060 (a surfactant, a product of Toho Chemical Industry, Co., Ltd., product name) were uniformly kneaded, granulated using a basket granulating machine, and then dried to obtain 100 parts of a granule.
- 2 parts of the compound (1217), 15 parts of the compound (3003), 58 parts of bentonite, 21 parts of talc, 1 part of dodecylbenzenesulfonic acid soda, 1 part of polyoxyethylene alkylaryl ether and 2 parts of lignin sulfonic acid soda were added, uniformly kneaded, granulated using a basket granulating machine, and then dried to obtain 100 parts of a granule.
- 10 parts of the compound (639), 30 parts of the compound (3007), 40 parts of diatomaceous earth, 5 parts of Sorpol 5039 (a mixture of an anionic surfactant and white carbon, a product of Toho Chemical Industry, Co., Ltd., product name) and 15 parts of white carbon were uniformly mixed and pulverized to obtain a wettable powder.
- 30 parts of the compound (3004), 20 parts of the compound (3001), 43 parts of kaolinite, 5 parts of Sorpol 5039 (a mixture of an anionic surfactant and white carbon, a product of Toho Chemical Industry, Co., Ltd., product name) and 2 parts of white carbon were uniformly mixed and pulverized to obtain a wettable powder.
- 10 parts of the compound (601), 5 parts of Sorpol 3074 (a nonionic surfactant, a product of Toho Chemical Industry, Co., Ltd., product name), 5 parts of a 1% aqueous solution of Xanthan gum, 40 parts of water and 10 parts of ethylene glycol were uniformly dissolved. Subsequently, 30 parts of the compound (3008) were added thereto and the resulting mixture was well stirred, followed by wet grinding with a sand mill to obtain a flowable formulation.
- 5 parts of the compound (3005) , 0.5 part of the compound (210), 94.3 parts of clay and 0.2 part of Driless A were uniformly mixed to obtain a powder formulation.
- Furthermore, to make sure that the insecticidal and fungicidal composition of the present invention has excellent insecticidal and fungicidal activities, the following test examples are illustrated. However, the present invention is not restricted to these test examples.
- Rice (cultivar: koshihikari) cultured in a nursery box was treated with a granule formulation of a prescribed amount, and then 4 seedlings thereof planted in a 1/5000a pot were transplanted to 8 pots. After 14 days from the treatment, canopies in 4 pots were cut and put into a plastic cup (diameter: 10 cm, height: 10 cm) along with 10 two-year-old larvae of Chilo suppressalis. After 4 days, the mortality was examined (4 replications). Furthermore, after 30 days from the treatment, the other 4 pots were put into an artificial weather chamber (set condition: 25 degree centigrade, 12-12 hr light-dark cycle), and a spore suspension of Pyricularia oryzae was spray-inoculated. The humidity at the weather chamber was kept high and, after 7 days, the number of Pyricularia oryzae lesions was examined. The control value was calculated according to the following equation (4 replications). The results are shown in Table 10. In the Table, gai represents the amount of active ingredients (g).
-
[Table 10-1] Supplied chemical Amount of treated chemical (gai/box) Mortality (%) Pyricularia oryzae Control value Compound 106 + Compound 3003 5+15 100 100 Compound 106 + Compound 3004 5+15 100 100 Compound 106 + Compound 3005 5+15 100 100 Compound 106 + Compound 3006 5+7.5 100 100 Compound 106 + Compound 3007 5+7.5 100 100 Compound 106 + Compound 3008 5+7.5 100 100 Compound 1217 + Compound 3003 5+15 100 100 Compound 1217 + Compound 3004 5+15 100 100 Compound 1217 + Compound 3005 5+15 100 100 Compound 1217 + Compound 3006 5+7.5 100 100 Compound 1217 + Compound 3007 5+7.5 100 100 Compound 1217 + Compound 3008 5+7.5 100 100 Compound 1245 + Compound 3003 5+15 100 10.0 Compound 1245 + Compound 3004 5+15 100 100 Compound 1245 + Compound 3005 5+15 100 100 Compound 1245 + Compound 3006 5+7.5 100 100 Compound 1245 + Compound 3007 5+7.5 100 100 Compound 1245 + Compound 3008 5+7.5 100 100 Compound 639 + Compound 3003 5+15 100 100 Compound 639 + Compound 3004 5+15 100 100 Compound 639 + Compound 3005 5+15 100 100 Compound 639 + Compound 3006 5+7.5 100 100 Compound 639 + Compound 3007 5+7.5 100 100 Compound 639 + Compound 3008 5+7.5 100 100 [0414] -
[Table 10-2] Supplied chemical Amount of treated chemical (gai/box) Mortality (%) Pyricularia oryzae Control value Compound 1246 + Compound 3003 5+15 100 100 Compound 1246 + Compound 3004 5+15 100 100 Compound 1246 + Compound 3005 5+15 100 100 Compound 1246 + Compound 3006 5+7.5 100 100 Compound 1246 + Compound 3007 5+7.5 100 100 Compound 1246 + Compound 3008 5+7.5 100 100 Compound 106 5 95 4 Compound 1217 5 95 0 Compound 1245 5 97.5 5 Compound 639 5 95 5 Compound 1246 5 97.5 0 Compound 3003 15 0 100 Compound 3004 15 0 100 Compound 3005 15 0 100 Compound 3006 7.5 0 100 Compound 3007 7.5 0 100 Compound 3008 7.5 0 100 Untreated plot 0 0 - A granule formulation of a prescribed amount was used in a submerged application for 4 pots of 1/5000a rice (cultivar: koshihikari; 4 leaf stage) pots. After 7 days from the treatment, canopies in 2 pots were cut and put into a plastic cup (diameter: 10 cm, height: 10 cm) along with 10 two-year-old larvae of Chilo suppressalis. After 4 days, the mortality was examined (2 replications). Furthermore, after 14 days from the treatment, the other 2 pots were put into an artificial weather chamber (set condition: 25 degree centigrade, 12-12 hr light-dark cycle), and a spore suspension of Pyricularia oryzae was spray-inoculated. The humidity at the weather chamber was kept high and, after 7 days, the number of Pyricularia oryzae lesions was examined. The control value was calculated according to the following equation (2 replications). The results are shown in Table 11. In the Table, gai represents the amount of active ingredients (g).
-
[Table 11-1] Supplied chemical Amount of treated chemical (gai/10a) Mortality (%) Pyricularia oryzae Control value Compound 106 + Compound 3003 300+450 100 100 Compound 106 + Compound 3004 300+450 100 100 Compound 106 + Compound 3005 300+450 100 100 Compound 106 + Compound 3006 300+225 100 100 Compound 106 + Compound 3007 300+225 100 100 Compound 106 + Compound 3008 300+225 100 100 Compound 1217 + Compound 3003 300+450 100 100 Compound 1217 + Compound 3004 300+450 100 100 Compound 1217 + Compound 3005 300+450 100 100 Compound 1217 + Compound 3006 300+225 100 100 Compound 1217 + Compound 3007 300+225 100 100 Compound 1217 + Compound 3008 300+225 100 100 Compound 1245 + Compound 3003 300+450 100 100 Compound 1245 + Compound 3004 300+450 100 100 Compound 1245 + Compound 3005 300+450 100 100 Compound 1245 + Compound 3006 300+225 100 100 Compound 1245 + Compound 3007 300+225 100 100 Compound 1245 + Compound 3008 300+225 100 100 Compound 639 + Compound 3003 300+450 100 100 Compound 639 + Compound 3004 300+450 100 100 Compound 639 + Compound 3005 300+450 100 100 Compound 639 + Compound 3006 300+225 100 100 Compound 639 + Compound 3007 300+225 100 100 Compound 639 + Compound 3008 300+225 100 100 -
[Table 11-2] Supplied chemical Amount of treated chemical (gai/box) Mortality (%) Pyricularia oryzae Control value Compound 1246 + Compound 3003 300+450 100 100 Compound 1246 + Compound 3004 300+450 100 100 Compound 1246 + Compound 3005 300+450 100 100 Compound 1246 + Compound 3006 300+225 100 100 Compound 1246 + Compound 3007 300+225 100 100 Compound 1246 + Compound 3008 300+225 100 100 Compound 106 300 90 3 Compound 1217 300 95 5 Compound 1245 300 95 0 Compound 639 300 90 0 Compound 1246 300 95 4 Compound 3003 450 0 100 Compound 3004 450 0 100 Compound 3005 450 0 100 Compound 3006 225 0 100 Compound 3007 225 5 100 Compound 3008 225 0 100 Untreated plot 0 0 - Insecticidal Test on Rice Striped Stem Borer (Chilo suppressalis) and Control Test on Rice Blast (Pyricularia oryzae) of Paddy Rice
A liquid chemical which was prepared to the prescribed concentration was sprayed on 4 pots of rice (cultivar: koshihikari; 4 leaf stage) pots. After air-drying, canopies in 2 pots were cut and put into a plastic cup (diameter: 10 cm, height: 10 cm) along with 10 two-year-old larvae of Chilo suppressalis. After 4 days, the mortality was examined (2 replications). Furthermore, after 1 day from spraying, the other 2 pots were put into an artificial weather chamber (set condition: 25 degree centigrade, 12-12 hr light-dark cycle), and a spore suspension of Pyricularia oryzae was spray-inoculated. The humidity at the weather chamber was kept high and, after 7 days, the number of Pyricularia oryzae lesions was examined. The control value was calculated according to the following equation (2 replications). The results are shown in Table 12. -
[Table 12-1] Supplied chemical Amount of treated chemical (gai/10a) Mortality (%) Pyricularia oryzae Control value Compound 601 + Compound 3003 100+150 100 100 Compound 601 + Compound 3004 100+150 100 100 Compound 601 + Compound 3005 100+150 100 100 Compound 601 + Compound 3006 100+60 100 100 Compound 601 + Compound 3007 100+60 100 100 Compound 601 + Compound 3008 100+60 100 100 Compound 1208 + Compound 3003 100+150 100 100 Compound 1208 + Compound 3004 100+150 100 100 Compound 1208 + Compound 3005 100+150 100 100 Compound 1208 + Compound 3006 100+60 100 100 Compound 1208 + Compound 3007 100+60 100 100 Compound 1208 + Compound 3008 100+60 100 100 Compound 210 + Compound 3003 100+150 100 100 Compound 210 + Compound 3004 100+150 100 100 Compound 210 + Compound 3005 100+150 100 100 Compound 210 + Compound 3006 100+60 100 100 Compound 210 + Compound 3007 100+60 100 100 Compound 210 + Compound 3008 100+60 100 100 Compound 3000 + Compound 3003 100+150 100 100 Compound 3000 + Compound 3004 100+150 100 100 Compound 3000 + Compound 3005 100+150 100 100 Compound 3000 + Compound 3006 100+60 100 100 Compound 3000 + Compound 3007 100+60 100 100 Compound 3000 + Compound 3008 100+60 100 100 -
[Table 12-2] Supplied chemical Amount of treated chemical (gai/box) Mortality (%) Pyricularia oryzae Control value Compound 3001 + Compound 3003 100+150 100 100 Compound 3001 + Compound 3004 100+150 100 100 Compound 3001 + Compound 3005 100+150 100 100 Compound 3001 + Compound 3006 100+60 100 100 Compound 3001 + Compound 3007 100+60 100 100 Compound 3001 + Compound 3008 100+60 100 100 Compound 3002 + Compound 3003 100+150 100 100 Compound 3002 + Compound 3004 100+150 100 100 Compound 3002 + Compound 3005 100+150 100 100 Compound 3002 + Compound 3006 100+60 100 100 Compound 3002 + Compound 3007 100+60 100 100 Compound 3002 + Compound 3008 100+60 100 100 Compound 601 100 95 2 Compound 1208 100 95 5 Compound 210 100 95 0 Compound 3000 100 90 3 Compound 3001 100 95 0 Compound 3002 100 90 3 Compound 3003 150 0 100 Compound 3004 150 0 100 Compound 3005 150 0 100 Compound 3006 60 0 100 Compound 3007 60 5 100 Compound 3008 60 0 100 Untreated plot 0 0
Claims (5)
- An insecticidal and fungicidal composition comprising;
one or two or more compounds selected from compounds represented by the general formula (1) or (2); and
one or two or more compounds selected from compounds represented by the general formula (3) or (4) as active ingredients,
a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group,
a pyridyl group, or
a pyridyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di C1-C4 alkylamino group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; and
Q2 is represented by the general formula (A),
a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group and a C1-C4 alkoxycarbonyl group,
a pyridyl group,
a substituted pyridyl group having one or more substituents selected from a halogen atom, a C1-C6 haloalkyl group and a C1-C6 haloalkoxy group,
a thienyl group, or
a tetrahydrofuran group); and
Q3 is represented by the general formula (B), - An insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (1) as set forth in claim 1 and one or two or more compounds selected from compounds represented by the general formula (3) as set forth in claim 1 as active ingredients.
- An insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (1) as set forth in claim 1 and one or two or more compounds selected from compounds represented by the general formula (4) as set forth in claim 1 as active ingredients.
- An insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (2) as set forth in claim 1 and one or two or more compounds selected from compounds represented by the general formula (3) as set forth in claim 1 as active ingredients.
- An insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (2) as set forth in claim 1 and one or two or more compounds selected from compounds represented by the general formula (4) as set forth in claim 1 as active ingredients.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005214743A JP4580836B2 (en) | 2005-07-25 | 2005-07-25 | Insecticidal composition |
PCT/JP2006/314246 WO2007013332A1 (en) | 2005-07-25 | 2006-07-19 | Insecticidal and bactericidal composition |
Publications (1)
Publication Number | Publication Date |
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EP1938685A1 true EP1938685A1 (en) | 2008-07-02 |
Family
ID=37683233
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP06781253A Withdrawn EP1938685A1 (en) | 2005-07-25 | 2006-07-19 | Insecticidal and bactericidal composition |
Country Status (8)
Country | Link |
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US (1) | US20090192167A1 (en) |
EP (1) | EP1938685A1 (en) |
JP (1) | JP4580836B2 (en) |
KR (1) | KR101004225B1 (en) |
CN (1) | CN101203132B (en) |
BR (1) | BRPI0613909A2 (en) |
TW (1) | TWI365713B (en) |
WO (1) | WO2007013332A1 (en) |
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WO2009080203A3 (en) * | 2007-12-21 | 2009-11-05 | Bayer Cropscience Ag | Aminobenzamide derivatives as useful agents for controlling animal parasites |
WO2010015355A2 (en) * | 2008-08-08 | 2010-02-11 | Bayer Cropscience Ag | Novel acylaminobenzamide derivatives |
US8853440B2 (en) | 2008-08-13 | 2014-10-07 | Mitsui Chemicals Agro, Inc. | Method for producing amide derivative |
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- 2006-07-19 WO PCT/JP2006/314246 patent/WO2007013332A1/en active Application Filing
- 2006-07-19 EP EP06781253A patent/EP1938685A1/en not_active Withdrawn
- 2006-07-19 BR BRPI0613909-4A patent/BRPI0613909A2/en not_active IP Right Cessation
- 2006-07-19 US US11/989,293 patent/US20090192167A1/en not_active Abandoned
- 2006-07-19 KR KR1020087002776A patent/KR101004225B1/en active IP Right Grant
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WO2010015355A3 (en) * | 2008-08-08 | 2010-12-16 | Bayer Cropscience Ag | Acylaminobenzamide derivatives |
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Also Published As
Publication number | Publication date |
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TWI365713B (en) | 2012-06-11 |
TW200744451A (en) | 2007-12-16 |
BRPI0613909A2 (en) | 2011-02-15 |
JP4580836B2 (en) | 2010-11-17 |
CN101203132A (en) | 2008-06-18 |
KR101004225B1 (en) | 2010-12-27 |
CN101203132B (en) | 2012-05-23 |
WO2007013332A1 (en) | 2007-02-01 |
US20090192167A1 (en) | 2009-07-30 |
KR20080027376A (en) | 2008-03-26 |
JP2007031324A (en) | 2007-02-08 |
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